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`EXHIBIT D
`
`EXHIBIT D
`
`

`
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`
`CRC Handbook
`
`of
`
`Chemistry and Physics
`
`A Ready-Reference Book of Chemical and Physical Data
`
`Editor-in-Chief
`
`Robert C. Weast, Ph.D.
`
`Associate Editors
`
`Melvin J. Astle, Ph.D.
`William H. Beyer, Ph.D.
`
`In collaboration with a large number of professional chemists and physicists whose
`assistance is acknowledged in the list of general collaborators and in connection with
`the particular tables or sections involved.
`
`@512‘;
`
`CRC Press, Inc.
`Boca Raton. Florida
`
`APOTEX_AZFL 0061946
`
`

`
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`
`°1974, 1975,
`
`l9’]r'6, 1977. 1978, I979, 1930, 1981, 1982. 1983, 1984, I985, 1986, 1987 by CRC Press. Inc.
`
`“I964, I965. I966. I967, I968, I969, I970, I971, 1972. 1973 by THE CHEMICAL RUBBER CO.
`Copyright 1918, [920 by The ‘Chemical Rubber Company {Copyright renewed I946, I948 by Chemical Rubber Publishing Company)
`
`I925 (Copyright renewed I953), I926 (Copyright renewed I954). 1927 (Copyright
`Copyright 1922 [Copyright renewed I950),
`renewed I955), I929 (Copyright renewed 1957), I936, I937 (Copyright renewed I965 by The Chemical Rubber Co.), 1939. 1940
`(Copyright renewed [968 by the Chemical Rubber Co.), 194i (Copyright renewed 1969 by The Chemical Rubber Co.),
`I942
`(Copyright renewed l9?0 by The Chemical Rubber Co.), 1943 (Copyright renewed 1971 by The Chemical Rubber Co.),
`I944
`(Copyright renewed 1972 by The Chemical Rubber Co. ), 1945 (Copyright renewed 1973 by The Chemical Rubber Co.), 194?, I949,
`I950, l95l,
`I952 (Copyright renewed [980 by CRC Press. Inc.), [953 (Copyright renewed [9813 by CRC Press. Inc]. 1954
`(Copyright renewed I982 by CRC Press, Inc.}, 1955 [Copyright renewed I983 by CRC Press, Inc.), I956 by Chemical Rubber
`Publishing Company
`
`'-'-‘I957, I958, I959. I960, I962 by Chemical Rubber Publishing Company
`
`Second Printing, 1987
`
`Ah‘ Rights Reserved
`Library of Congress Card No. 13-11056
`PRINTED IN U.S.A.
`1snnos493-04453.7
`
`AP OTEX_AZFL 0061 947
`
`

`
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`
`those of the natural hormones.
`
`STEROID HDRMONES AND OTHER STEROIDAL SYNTHETICS
`Compiled by Erwin Di Cyan. Ph.D.
`The held of steroids has expanded considerably and rapidly in degree and in kind._bccause synthetic steroids have been
`synthesized which though resembling the hormones in the body have no natural counterpart. but exert an effectcomparable to
`‘In fact. the terrn steroidhormone thus becomes a misnomer when applied to the newer synthetically prepared steroids which
`do not have a counterpart in the body of man or other animals——as prednisone. (A hormone. by definition, is a material with
`certain functions -and characteristics, secreted by the ductiess glands. That part of the definition cannot be met by prednisone
`or by similar steroids as these are not secreted by the ductless, or endocrine glands.)
`All the hormones as well as the synthetic analogues have In common the cyclopentanophenanthrene nucleus. Although
`chemically very similar. a comparatively slight structural change is in many instances productive of substances which have
`physiologically dissimilar effects.often acting upondifferent physiologicsystems. But in many casesasmallchangein structure
`will result merely In an accentuation ofcertain effects.
`
`'
`
`emales:
`
`The Cyclopentanophenanthrene Nucleus
`Classification. Classification becomes a bizarre problem by reason of the la) overlapping uses to which these substances
`are put. and lb) the multiple purposes for which the hormones or synthetic substances are used. Indeed. the steroids may be
`classified by structure; that however would be uninformative to the student as to their use. Classification by origin.as adrenal,
`would also be unsuitable because. for example.a number of the adrenal corticosteroids are not _l‘ound in the adrenal cortex
`2
`e
`.
`erel
`resemble the natural hormones found in the adrenal cortex.
`For those reasons the hormona or o " - -
`- '
`=
`‘
`-
`.=
`- -.
`9
`.-—.
`.
`- milled b -and—large, by their predominant phar-
`macologic effects. Even that classification has its disparitiesas for example, the use o male sex hormones. i.e.
`-
`.
`a
`a 1'
`- .
`is neither limited to men. nor to uses which entail their effect upon male sex characteristics.
`Uses. Originally. the use of steroid honnones was largely based upon one or more of the following predicates:
`(a) To supplement the progressively decliningsecretion ofa specific hormone due to natural biologic aging ofthe organism;
`in the menopause as an example of such declining secretion. :1 female sex hormone is used for such supplementation:
`lb) To make available to the body a specific hormone. the natural secretion ofwhich is inhibited because ofa conge ’
`developmental anomaly;the underdevelopment ofmale secondary sex characteristics is an example of such an Inhibited
`gecretion. in which a male sex hormone 15 used-—and correspondingly. female sex hormones in underdevelopment in
`{c} Tocause a reversal ofhormonal balance in the treatment ofdiseases peculiar toa sex; for example, in the case ofcancer
`of the female breast. a male sex hormone is administered , and in cancer of the prostate. a female sex hormone is used;
`(til To mimic a natural function. as menstruation, by the administration of estrogens——on withdrawal of which bleeding
`occurs; or by the alternate use of estrogenic and progestational—both female sex hormones.
`(el To delay a function. as ovulation. as in oral contraceptives. or birth control pills.
`Since the finding that cortisone ameliorates the symptoms of rheumatoid arthritis (1949) the adrenal corticosteroid hormones
`and especially the synthetically prepared steroid analogues which have no natural counterpart in the body. have been success-
`fully employed in the treatment of diseases not related to sex or sex function.
`Antlrogens and Anabolic Agents.
`.
`he tables under this classification have the effect ofmale sex hormones
`(androgens)i.e.. to stimulatesexual maturation, in
`‘
`'
`' " etc. Butall andro ens havein greater orlesserdegree
`the ability to stimulate muscle development, i.e.. an anabolic effect. Among the syuthetica ly prepared agents which have no
`counterpart in the body {Methandrostenolone or Oxymetholone} are those which have a lessened androgenic. buta heightened
`anabolic effect. These qualities are determined by biological tests on animals but principally confirmed by clinical use in man.
`The anabolic efiect includes remineralization ofbone. which may be partially den-iineraliacd (osteoporosis) by age. or by certain
`drugs. as the adrenal corticosteroids (q .v.}.
`~
`Anabolic agents are used for muscle and bone nutrition in men as well as women. The reason for the high interest in synthetic
`steroidal substances for anabolic use. is based on the need for materials. which within a given effective dose have a greater
`anabolic-to-androgenic ratio than such androgens as methyl testosterone. Otherwise. the administration of androgens to
`women produces manifestations of virilism. such as growth of hair on the face. a deepening of the voice. etc. Androgens are
`also used in the female in the suppression o
`‘
`g and in the treatment of cancer of the breast and cervix. (For
`other androgen-like agents. see also Progestogens and Progestins.)
`Estrogens. Estrogenic agents hasten sexual maturation in the female. Therefore. they are used in ttnderdevelopment in the
`female. The widest use ofestrog
`fthe menopause. in which they supplement from without. the secretion
`_
`of natural estrogens by the ovary,
`is usually a slow process.
`and the declining secretion gives rise to various
`'
`‘
`'ustment to the
`new status takes pl
`’
`'
`'
`'
`‘
`Frequently. a menopause must
`tion or by the removal of the uterus. Severe vasomotor 5
`—among other drugs—are used in the amelioration to these symptoms.
`Estrogens (e_special1y diethylstilbestrol which though not a hormone has an estrogenic effect) are also used in the control
`ofcfinnicroil‘theprostate in the male. Note the inverse correspondence totheuse ofmale sex hormon:’i:i’;ancer ofthe breast
`ll'll. e ema e.
`'
`Prngestogens and Progestlls (Including 19-Norsterold Compounds). The agents under that listing nclude progesterone. a
`female sex honnone. as well as progestins. i.e.. synthetic progesterone-like compounds which have no natural counterpart in
`the body. Their use includes a variety of conditions: functional uterine bleeding. absence ofmenstruation (amenorrhea) used
`at times with estrogens, painful menstruation (dysmenorrhea). infertility. habitual abortion in order to maintain pregnancy.
`and in fact. to suppress ovulation hence their use as antifertility drugs. Certain pt‘ogeslins——-as not-ethindrone combined with
`
`C-632
`
`APOTEX_AZFL 0061948
`
`

`
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`STEROID HORMONES AND OTHER STEROIDAL SYNTHETICS (Continued)
`
`an estrogen, are the principal components of birth control pills—suppressing ovulation. there is no egg to fertilize. hence con-
`ception does not take place.
`Adrenal Corticosteroids, Ilchlllng Antllnflnnnatory, Antlnlergic and Antirlielmatlc Agents. The adrenal cortex secretes a
`large-number of hormones. They usually difler from each other in the accentuation of some phases of their properties. Virtually
`all of the cortical hormones are catabolic, thus having an effect in this respect,_diarnetrically opposed to the androgens which are
`anabolic. Nearly all the cortical hormones—differ-ing in degree from each otJ1er—cause retention of sodium and water by the
`body and hasten the excretion of potassium. These effects are utilized in the treatment of adrenal insufliciency or Addisorrs
`disease, in which conversely, there is an undue excretion of sodium and a strong retention of potassium. Desoxycorricosterone
`is used in Addison's disease because it has a particularly strong sodium retaining and potassium excreting elfect.
`Since the finding in 1949 of the usefulness of cortisone in profoundly reducing the symptoms of rheumatoid arthritis. the
`adrenal corticosteroids, including hydrocortisone. a natural hormone secreted by the adrenal cortex, and particularly the
`synthetic analogues not found in the body, as prednisone, have been used in the treatment of a wide variety of inflammatory
`diseases—especially diseases of collagen tissue. The same antiinflammatory effect is also brought into use in the reduction of
`infiammations associated with diseases of the skin. allergy. asthma. and in such systematic diseases as disseminated lupus
`erythernatosus. also a collagen disease.
`The drawbacks of cortisone. also shared in lesser measure by hydrocortisone. gave the impetus to the synthesis of steroidal
`substances not native to the body but differing somewhat from cortisone and hydrocortisone. in order to reduce the drawbacks
`attendant to the use of the latter. The sideefi'ecr.s-
`-especially those of cortisone—are retention of water and sodium. excretion
`of potassium. loss of mineral from bone leading to osteoporosis and fractures. hypertension. at times diabetes. personality
`changes or gastric ulcer. Prednisone and prednisolcne among others (see tables) are two such steroidal synthetics which have
`the effects of cortisone, but fewer or less severe sideeffects. Whereas the synthetic steroidal substances are so
`rior to cortisone
`wiiah respect to lessened sideelfects. it cannot be said that the sideefiects are absent—rhey vary in degree rorn substance to
`so stance.
`Diuretic. Antidluretic and Local Anesthetic Agents. Aldosterone. a natural hormone of the adrenal cortex promotes retention
`in the body of sodium and water, and facilitates excretion of potassium. Hence its eflect is almost diametrically opposed to
`diuretic-s—especially the thiazide diuretics. Aldosterone is much more active in this respect than desoxycorticosterone. and is
`used in the treatment of Addison's disease. a hypofunction of the adrenal glands.
`Spironolactone is an antagonist to aldosterone—the latter when elaborated in the body in excessive amounts gives rise to
`a syndrome called aldosteronism. Spiroriolactone. a synthetically produced steroid does not have a natural counterpart in
`the body, is diuretic when mercurial or thiazide diuretics are inelfective ; it prevents sodium retention and potassium excretion-
`'0
`us
`7
`-.
`eflects o posits to aldosterone. ll-Ience spironolactonc is used in aldosteronism, against _edema, in the treatment of congestive
`
`Doses. The amount of substance which comprises a dose of steroid hormones. or of the steroidal synthetics varies from
`substance to substance—from 0.1 mg for an estradiol ester, to 50 mg for a I9-norsteroid compound. The dose is conditioned
`upon the order of activity of the substance, the purpose for which it is administered. as well as the patient's response. How-
`ever. as additional steroids for hormonal use are synthcsi2cd—csp-Ecially those with adrenocortical activity. their average dose
`is usually smaller than the
`reviously available steroid. The smaller effective dose of the more recent steroid is cited as an
`advantage over the previously available steroid.
`However. a smaller dose cannot be claimed as an inherent advantage of a new steroid in comparison with an existing one,
`unless the lower dosage exhibits either greater or more prolonged activity or lesser sideeffects. One cannot meaningfully compare
`a dose, milligram for milligram. without taking into consideration if a hei hteoed effect of the smaller dose produces fewer
`sideeffects. For example, it does not make any difference if a Riven effect an the same accompanying sideeflects are produced
`bya 50mgora5 mgdose.
`
`ADRENAL CORTICOSTEROIDS, INCLUDING ANTIINFLAMMATORY, ANTIALLERGIC
`AND ANTIRHEUMATIC AGENTS
`
`sermvrsruasoive;
`93!-1'ltI0l’O-lfifl-metllylprednisolone;
`l5.B-l'|'l¢ll'l3I'l-I I 5. I 7:12 I -trih,ydroxy-9a-
`fluoro-1.4-pregnadiene-3.20-dione.
`
`BETAMETHASONE ACETATE:
`9a»_fluow- I 6,6’-rnethylprcdnisolovric-2 I -
`_aoerate.
`I
`
`BETAMETHASONE DISODIUM
`PHOSPH ATE;
`9a-fluo to-I613-methylprednisolonc-ll -
`diwdil-1|'l'l Ph05Ph31¢‘--
`
`HaifopoaNil:
`
`Melting point
`(“Cl
`
`{a1§+II'2to +120tI0omg.in romi.
`dioxanel
`
`[u)§+r2cto +I2srIuomg.'in1oml.
`dioxancl
`
`t_¢}2T:3-99tD +I0$(10I:I mg. in to ml.
`watcrl
`
`Absorption
`max.
`
`239 my, EU ':{,.
`
`I cm] 390. methanol
`
`239 mp. methanol
`
`24l my. water
`J"
`
`APOTEX_AZFL 0061949
`
`

`
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`
`smnom HORMONES AND OTHER STEROIDAL SYNTl{EI'l(S (Confined)
`
`Names at
`synonyms:
`
`CHLOROPIIEDNISONE
`ACETATE;
`Ga-chlomprednisonc aczlate;
`6w-chl0l'0- :3‘ "-pregnadicn-I 712,21 -
`dial-3.! 1.20-triomc 2|-aceute.
`
`CORTICDBTERONE:
`I l,2I~di|1ydloxyprogesmerone;
`1!“-pmegnema-l 1 ,B,2I-dial-3.20-dione;
`I 13.2 I -dihyd.r0xy-I-p'regncnc-3.20-
`dione:
`Kendal] compound B; Reichstein
`substance H.
`
`CORTIBONE:
`IT-llydroxy-I ldehydmwrticomrom:
`lTu.2!-dfhydrnxyvt-pmpn:ne-3. I1 .20-
`Lrionc:
`A‘-pregnant-£13.21-diol-3.!1.20-Irione:
`Kendall compound E; Winlcrsteincr
`compound F.
`
`M giecular
`we@t
`
`Melting" point
`(“Cl
`'fi
`Pfgiafim
`
`5
`
`Absorplion
`IIIBJI.
`
`Name-.38:
`synonyms:
`
`Moiecuiar
`weigh!
`
`Melting poim
`(‘Cl
`
`TOWIIEOI1
`5”°°ifi°
`
`Absorption
`max.
`
`.
`25
`(g)E.+I-31:0 + t-mum mg. m
`I0 ml. chloroform]
`
`23'! my
`
`DESOXYCDRTICDSTERONE;
`deoxsmmfioosumm;
`I I-desoxyoombustcrone;
`2] -hydrouyprugesterorle;
`4—pregnen-2 I-at-3.20-dione:
`Randall GBIDXY compound B:
`Reichstein subsixltce Q.
`
`DESOXYCORTICOSTERONE
`ACETATE;
`DC.+\;
`I I-desnxycoriiomtcronc acetate.
`
`DESOXYCORTIOOSTERONE
`PIVALATE:
`desoxyuanicnatnrnne u-imecltylaceme:
`21-hydraxy~4-presncm—3.2o-djone
`pivalate.
`
`.
`
`,c
`
`o
`
`330.2
`
`name:
`
`cH.on
`o':=o
`
`H 3C
`
`CHHMOJ
`
`0
`
`I
`
`rm:
`
`372.4
`
`us-Han
`
`ll0
`C COCH:0CClCH;la
`
`H
`
`’
`
`C2 DHJIOI
`
`¢
`
`CI‘I;00OCl'l.a
`'=o
`
`BC
`
`o
`
`Cllflliol
`
`H
`
`414.6
`
`|9s—zo4
`
`1
`
`<a>§+n5_ +11s(:oomg.in1omi.
`alcohol]
`
`Ea)2—[2+lfi8— +l'a‘8[1D0mg. in mm.
`diosanel
`
`[u}%+15'!14t]3r,;indiox2ne}
`
`240 1'n,u{i.n ethanol]
`
`APOTEX_AZFL 0061950
`
`

`
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`
`STEROID HORMONES AND OTHER STEROIDAL SYNTHETICS {Contlllileifi
`
`DEXA METHASONE:
`hexadecadrol:
`9m-fluom-16¢-methyl predmisolone;
`9:-fluoro-l1.B,l‘fu-2]-u-ihydmxy-16¢~
`rneihgrl-l.vI-praguadime-3.20-dim1c;
`16¢:-melllyi-‘Ia-fluoro-I .4—pm:nad‘sene-
`I I H. I Tu-2|-trial-3,20-dione:
`16.:-methyl-9:-lluotovd‘-hv:tI*ooo1lisone:
`I ~dehyd'ro-l6¢-mathyl—9¢-fluamhydro-
`cortisone.
`
`DICHLOR ISONE ACETATE '.
`9:-l I 5-d 'ncln1ora-l,4-preymdiena-
`l 11.21 -dioI—3.20-d‘mne—1l-acetate
`
`FL UOCIND LONE ACETONIDE;
`6a,9n:—difluoro-16¢ hyd;-uxypu-adnim1gn,.|g_
`IT-aoetonide:
`6cx.9u-difluoto-16a,lT¢—i!0flr0P?lidu1ndiogy-
`L4-Dltsnadiene-3.10-alone.
`
`'
`
`CnH:oFDs
`
`Melting point
`(‘CI
`
`{:1}
`
`+18 um mg.'n110 ml. dioxanci
`
`max.
`
`I
`
`I
`
`‘
`
`255-266
`
`25
`{cl 6 + I60 — In-S [I00 mg. in II) ml.
`dbnml
`237mg:-3l6—33?(c{}
`
`Q
`I
`no: less than +95“ and not more than
`+105 C at 25 C.
`N 23Tm,u1-Imp
`
`FLIJOROHYDROCORTISONE:
`fiudrooonisone;
`9d-fluorohydrocortisone:
`91-fluorocortisol;
`fluohydrisonc;
`9.:-fluoro—l1.8.11u,1i-Irihgrdroxy-IL
`pregnene-3.20-diune:
`9ut-fluom- IT-Ilydtonycorticosleronc.
`
`FLUOR.0ME"|"'HClLONE:
`9::-fiuorc-—l 13.1‘.-‘a:-dihydroxy-6w
`mcihyl-I .4-pregnadiene-3.20-dionc:
`2|-desoxy-9a-flunro-6m-mcthyb
`prudnisolone.
`
`I-'-‘LUPREDNISOLONE:
`6:-fluoroprednisolone;
`fem-fiuoro-I-dehydrolzydmcortisone:
`on-fluor0—l 1.(I.ITa.2l -trihydroxy-I .4-
`Pfeslindiene-3.20-dione.
`
`(El-I;OI-I
`C=0
`. ..
`
`sC
`
`260-162idea.)
`m g + :39 :55 mg. in IIJ ml. alcohol}
`
`1
`
`29otc1ec.:'
`my gun (pyridine)
`239 mu ta. -« 15.050‘! methanol
`
`mp +33 {dioxane}
`im, 24!“! mu (I:
`|6.0C0]
`
`APOTEX_AZFL 0061951
`
`

`
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`
`STEROID HORMONES AND OTHER STEROIDAL SYNTHETICS (Cuntinued)
`
`Na mes 5‘:
`synonyms: '
`
`FLURANDRENOLONE:
`6-fluoro-I 6¢-hydrox5rhydrooorIis.Dne-
`I 6. I 7—auemI1ide:
`6:-fiuoro-I1,fl.2l-del1ydroxy-l6o..I7a-
`isopmpy [idcnediaxy-prcgna-4-cue-3.
`2:0-dione.
`
`HYD ROCORTESONE;
`cortisol:
`1?-hydmxycorlimslemne:
`hydtooortisnone Free alcohol:
`] I _B. l’?¢.1I -triI1ydroxy~4-prcgnene-J.2D-
`d-ione;
`4-presrIene- I l,s.1?a.2i-uriol-3.20-dicme:
`Kendall compound F; Rzichstein
`substance M.
`
`HYDROCORTISONE ACETATE:
`oort isol acetate:
`hydroconisone-21-acetate:
`I 1-hydruxycoriicostcrone-2| -acelale.
`
`Mulecula I
`weight
`
`Melting point
`
`362.5
`
`315-220 Nice.)
`
`+145u °,,+n cues;
`
`{-1} 255+:so— + :55 ['|U3mg. in mm:
`dioxane}
`
`is‘: El-)5—+ I5B-- 4- I65 (I00 mg. in iflrnl.
`dioxanel
`
`absorption
`max.
`
`236 m:.c{rnethanoIa
`
`242 mp
`
`241 mu (me! hanall
`
`Mama: at
`synonyms:
`
`HYDROCTIRTISONE SODIUM
`SUCCINATE:
`1 I11, I11, 2|-lrihydroxy-4-pregncno-3,
`2.0—diotIc. 2| hydmyun suu:-inate.
`sodium salt:
`hydrocortisunc, 2! hydrogen suutinalc.
`sodI'u111 salt.
`
`MET!-IYLPREDNISOLONE:
`an-rnalhylprrad nisolonei
`A‘-6:-methylhyd Iocortisone;
`I-dehydro—5u~mcIhylhydrooortisone:
`I I ,8. 1?g;.21-n'ihydroxy-6u-methyl-
`I .4- pregnadiene-3.‘20-dionc.
`
`MET1-I YLPREDNISOLONE SODIUM
`SUCCINATE:
`I-dehydro-in-Inethyfhydrocortisone.
`Ebhydmgen suocinate. sodium sall:
`6m-methylprednisolone 2|-hydrogen
`succinalc. sodium salt:
`llfl. |'?a. 21-Irihydroxy-6a—melhyI— I.
`4-pmgnadime-3. 20-djone. Zbhydrogen
`suocinate. sodium salt.
`
`"I-'H10¢lZI‘CH;CH;CO;Na
`C300
`
`(|3H;O(l3|CH;CH,C0:Na
`c=oO
`-----on
`
`:
`
`Moiecnlar
`weight
`
`Melting point
`(“C i
`
`Specific
`rotation
`
`Absorption
`max.
`
`(3),, 4 M-0 :5 talcahoil
`
`J2‘: ml“ [6 I5’-Foo}
`
`a;‘,,H,.,o.
`
`I 230-240 idea!
`
`{oz} -1%:-+85 tdioxancl
`
`4%-5
`
`dovcom pom
`
`(-219 +100 :4 laicoboll
`
`A “"242
`
`it HHSOD‘
`
`:4
`
`APOTEX_AZFL 0061952
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 9 of 20 PageID #: 1685
`Case 1:14—cv—O1453—LPS Document 48-6 Filed 11/23/15 Page 9 of 20 Page|D #: 1685
`
`STEROID HORMONES AND OTHER STEROID.-H. SYNTHETICS (Continued)
`
`Names &
`synan yms:
`
`PARAMETHASONE:
`6¢-fiuo1'o- léu-methylprednisolone ;
`fie:-liuoro-1 I 3-} Ta:.2I-trihydroxy-I 641-
`mcthym.4-prcgnadienc-3.20-dione.
`
`PARAMETHASONE ACETATE;
`Ga-flu om-16¢-methylpredn isotom-2| -
`acetate;
`6u-fluai1J-l6¢-methylpregna-l,4-die:Ie-
`I lfi.2l—d’iol-3.20-c1ionc~2|-aoelmzc:
`6a-fluom-IT,fl.l ?a,2 I -trihyd roxy-I 6a~
`m=thr|-|.4-pren:1adiene.3.1o-diom:.2I—
`acetate.
`
`PREDNISOLONE:
`metaoortandralone;
`5‘-dahydmooniaol;
`delta F:
`A‘-Ilydrooorlisone:
`A‘-dehydrohydrooorlisone;
`1.4-preanadiene-3.20-dione-1 I 3.1':.:.21—
`trial;
`I
`I 3. I 7.1.2 I-trihyd rmty-I .4-pltgn audienc-
`.?.‘_*G—ciinnc
`
`KJ3—244s
`
`+3910 +69 al 25°C
`
`{u]§+721’1 °,', in CHCL]
`D
`
`Hal} -1
`|__e__
`240 Mac.)
`I
`
`(¢}2—[:+97— +EO3{ICK!l mg. in 1033!.
`dioxanei
`
`242 my lmethanoi}
`
`H
`
`242 !l1p is = IS.000#n1cthanol
`
`Melling pom:
`(“Ci
`rolalion
`
`ITIQIX.
`Absorption
`
`Names &
`synonyms:
`
`PREDNISOLDNE PHOSPHJKTE SODIUM:
`disodium prednisolonz-. 2l—phos;:ha1e.
`
`PREDNISOLDNE PWALATE:
`prednisokme trimcthylacetnte:
`I15,17u.2l-trihydroxsh1.4-pre[:nudienc—3.2€I-dione 21-pivalate.
`
`COCI-I;_0CC[CH,|,
`....OH 9'
`
`C
`
`C,.H,.Na;O,,P
`
`M I nlccu Lu
`weight
`
`Melting pc-inl
`PC}
`
`Specific
`relation
`
`Absorption
`ITIZX.
`
`4- 1633411] °«_ fin dioxane}
`
`24-0 and 263 my {in absolute ethanol]
`
`APOTEX_AZFL 0061953
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 10 of 20 PageID #: 1686
`Case 1:14—cv—O1453—LPS Document 48-6 Filed 11/23/15 Page 10 of 20 Page|D #: 1686
`
`STEROID HORMONES AND OTHER STEROIDAL SYNTHETICS (Cnn1inued}
`
`Names at
`synonyms:
`
`PREDNISONE;
`melaomfandricin:
`a '-dehydrmofliamm:
`delta E:
`A '-cortisone :
`I.-I-pregnm:liene~lTn.2l-diol-3,11.20-trione:
`!':'a:.2 I-dihydroxyd,-II-pre3;o1adicnc—3.l 1.20-trione.
`
`TRIA MCINOLONE:
`9¢-fiunm-I6:-hydroxyprednisolona:
`Slaufluoru-I I fLI6a. I 1'u.2l-Inetrnhydroxy-I ,4-pregnadieI1e-
`3.20-dione.
`
`(EH30!-I
`=0
`--OH
`
`:5
`
`Molecular
`weight
`
`Melting point
`['0
`
`Specific
`rotation
`
`Absorpiinn
`ITIHX.
`
`358.4
`
`225 (dam
`
`.
`.
`25
`{on B + I6‘.-‘ — + H5 [I00 mu. an I0 ml. dmxane)
`239 my I: = 15.50|JImctI1anDl
`
`260--262.5 Mac.)
`
`25
`ta! 5 #51200 mg tn 100 ml— acetone!
`2.38 111.1: In - [$300)
`
`TRIAMCINOLONE ACETONIDE:
`9a-fluoru-I I 37.1 I-dil'Iyd.l‘0xy~l fiu,I 7¢-isopl'0p3I'lid¢l'Ie-
`diuxy-1.4-pre¢nad:'en¢-3.20-dione:
`9;-fluoro-lfiuhhydrmtypredniso-{one I6. IT-acctonifle.
`
`TR IA MCINOLON E DI:-\CE.TATE:
`l6¢.2 I-diacetouy-hvfiuorcr I I H. l?e:-dihydrnxy-lab
`ptegnadiene-3,20-dione:
`9nr-fiuuro-16¢-hydmnyprednisolorle |6.2l-diaoelate.
`
`H10C0CH,\
`=0
`
`CI-CH1 |Fofi
`
`2’N—2TB (dun): 292-294
`
`variable: |S8—'.'.35
`
`Absotptiun
`mu.
`
`(1);; + I09 — +1 12 £53.‘? mg. in ID ml. chloral‘-Jrrn]
`238-239 mp: {: - H.600}
`
`23
`D
`la} -~ +22 {T83 mg, in !0 I'|1I. chloroforrrlln
`239 mu [2 - |'5.2D|JI
`
`APOTEX_AZFL 0061954
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 11 of 20 PageID #: 1687
`Case 1:14—cv—O1453—LPS Document 48-6 Filed 11/23/15 Page 11 of 20 Page|D #: 1687
`
`STEROID HOIMONES AND OTHER STEROIDAL SYNTI-IETICS (Confined)
`ANDROGENS AND ANABOLIC AGENTS
`
`A N DROSTE RON E:
`cis-a nd rosiemnei
`3»:-Ilydruxy-l‘.'-androstanonc:
`andmsaanca n:—a]—l‘?om.
`
`FLUDXY MESTERONE:
`9::-fluom-I I fl—|1ydwxy- Ha-
`melhyltestosterone
`'
`9n:—fluom-I I,G.1 11?-dihydroxy-I Ta-
`melhyl-4-androsten-3-one.
`
`ALDDSTERONE;
`electrocortin;
`I E-oxoonrticoslerone 1
`I8-fonnyl-I1,fl',2l-diI1ydruxy«4-
`pregnant 3.21]-dimle.
`
`C:oHnF0:
`
`360.4
`
`270 idea.)
`
`I0!-—| I2 lllydralel: I64 Ianhydrous]
`
`{an} g+35- +90 (moms. in
`IO ml. dioxanll
`
`{.2} + II}? — + I09 {alcohol}
`
`_
`25
`(ml -6 H6] H0 1113. In l0‘n1L
`chloroform
`
`24-0 mp: [103 c — 4.20 monohydn:
`c mol. I 5.000 anhydm
`
`HYDROXY DIONE SODIUM:
`2 I —hydroxyprcgna n¢~3 .20-dionc—2 !—sodium
`hanisuccinate.
`
`SPIRONOLACTONE:
`3-(3-o no-‘I:-acely1lh|o— I ?;§—hydroxy—4-andruslcn— I ‘Fa-)'| :-
`pmpionic acid -; lactone.
`
`1'0
`
`Specific
`rotation
`
`Absorption
`llllx.
`
`Names 5:
`synonyms:
`
`Formulae:
`
`Cl-l;DCCH,CH;(:ONa
`II
`I
`ll
`0
`C=O 0
`
`C',,H;..0..Nu
`
`Meliing point
`(‘CI
`
`Ev-ccific
`rotation
`
`Absorption
`max.
`
`I93 -203 {deg}
`
`m g +95 {r:|IIaroI’orm) rm free acid.
`280 mu In = 932}
`
`-‘I-|6.S
`
`I35 {preliminary} 302 idem}
`
`25
`[1)--[-) — 34 ichlumronnl
`+93" = 10.200
`
`APOTEX_AZFL 0061955
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 12 of 20 PageID #: 1688
`Case 1:14—cv—O1453—LPS Document 48-6 Filed 11/23/15 Page 12 of 20 Page|D #: 1688
`
`STEROID HORMONES AND OTHER STEROIDAL SYNTHETICS _(CnntInI.Ied)
`
`‘Names 6:
`synonyms:
`
`METH ANDROSTENO LONE:
`17m-methyl-I13-hydroxy-I.+
`androstadien-3-one.
`
`METH ‘(LAN DR OSTEN EDIOL:
`MAD:
`metlmndriol:
`|?:I-1'nelh3'l-§—nndrosten-3,8. I 715-
`dial.
`-
`
`M ETH YL TESTOSTERONE:
`IT-methyl testosterone:
`I Tnemelhyl-5‘-arldrosten-I 1‘-.0-oi-3-on: :
`17¢ ,6I-hydmxy-l7(a-methyl-4-andrnsten—
`3-011 3.
`
`Melting point
`t°Cr
`
`[u)%’+'9— +1"Hl(X}mg.i.n 10 ml.
`alcohol)
`
`Int)1—[:—'.-'3 (I00 mg.irl I0 mI.n|cohcrI)
`
`[ill-I-69- +?5 [I00 mg. in 10 ml.
`dioxane}
`
`NORETHANDROLONE:
` m'
`I1"e:-ethyl-IT-hyd raxy-4-nora ndrosten-J-one;
`I 7::-eI.I:yl— I T-hyd raxy-I 9-norandrost-4-en-3-one.
`
`OXANDROLONE;
`11.8-hydroxy-1 1':-methyl-2--:-xa-Sa-andromnc-3-one.
`
`Melting point
`("Cl
`
`sprfigfion
`Absorption
`max.
`
`tut} 2-; +21 ldioxanc}
`240 mg; is = 16.500)
`
`Ia! %~2'I (I ";, in chloroform:
`None
`
`APOTEX_AZFL 0061956
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 13 of 20 PageID #: 1689
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`
`STEROID HORMONES AND OTHER STEROIDAL SYNTHETICS (Continued)
`
`UK‘? M ETHDLDNE:
`1 13-hydxoxy-2-hydIoxyIneIhy1ene—I?¢—me:hyI-3—andros|anone;
`2-hydr0:y1n.ethyIene~lT-m-methyl dihydrnlcslnslcronc.
`
`PIICIMETHU LONE:
`Ia-methyl-dihj-dm—les1ostemne pm pionate;
`Zn-melhyldu-andloslanca I 73-cl-3-one-propio naae,
`
`Molecular
`weight
`
`Meitirtg point
`I‘ Cl
`
`5'’“‘'‘“°
`mini“
`Absorption
`max.
`
`Names 5:.
`synonyms:
`
`Molecular
`weight
`
`Melling point
`P C}
`
`S
`
`if!
`”:’§m°i°n
`Absorption
`max.
`
`(.1! E = +3u2oo mg.i|: no ml. dimume]
`D
`E} = 54'! at 315 my (in alkaline methanol made 0.0] N with
`Na0I-I)
`
`:1;
`
`E-1-22- +29(2Dl] rng_in I0m|.chlorof'on11l
`without significant absorption from 220-300 my
`(nselhanol)
`
`TESTOSTE RONE;
`trans-testosterone;
`:1“—a11drnsten- I T-,0-ol-J-one:
`I ‘M-hydroxy-4-anclrtnsoen-3-one.
`
`TESTOSTERONE CY PIONNTEL
`testosterone cyclopentylp ropion ate:
`ITH-hydroxy-4-androsten-3-one. cyclopemanepropionaie.
`
`/cu,
`ow fi[QH:I:—(|1H Win;
`0
`CH3—CHI
`
`.
`24
`(ml -5 + I091400 mg. m Io ml. ancohon
`233 mp
`
`m, + 33.5 I 3.5 -:CH-Cl ,a
`Jm241 mp-ta NLI25}
`
`APOTEX_AZFL 0061957
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 14 of 20 PageID #: 1690
`Case 1:14—cv—O1453—LPS Document 48-6 Filed 11/23/15 Page 14 of 20 Page|D #: 16977‘
`
`STEROID HORMONFS AND OTHER SFEROIDAL SYNTHETICS {Cont'lIued)
`
`Names Jr.
`synonyms:
`
`TES'I'O$TERONE EHANTHATE:
`aeslastemne heptanoauc;
`I ‘F,d—hydrox5rand'rost—4—en-3-one- I 7-
`enanIhaIe_
`
`TESTOSTERONE PHENYLACETATE:
`I73-hyd roxy-iwanclrosten-3-one ph-en}-I-
`acaute;
`Iesmaiatone rlolnale.
`
`'T‘I':3'l‘OSTERONE PROPIONATE:
`a_\‘-androstezle-I 7-F-|'.Ir0pIionaIe—3-one.
`
`Melting point
`(‘{3}
`
`2-11 mg (in ethnnoli
`
`EQUILENIN :
`3-hydroxy»!?—keIu-1'-’-" “'-""
`astray-entaene:
`I.3.5—l0.6.E-esu-apenucn~3-
`oI— I ‘atone.
`
`ESTROGENS
`
`EQUILIN:
`3-I1ydmxy— I 7-kelo-:1 '--‘J’ '°'"
`cstratetracne:
`I .15.?-est rn [clraen-3-o|- I ‘I-one.
`
`+83— +90(I00mg. in Ioml.
`(mp
`diona nu}
`
`EBTIIA D301. {formerly called
`nvestradio I] :
`,8-estradiol:
`dihydmrolliculin:
`diliydruxycslrini
`1.3.5-estratriem.-3.l‘J'_a-dial;
`3.1 Ldihydroxy-A ' '”‘ “’-eslratrietle:
`3. ['1-cpidiflydmxycslralricue.
`
`H
`
`HgC 0
`
`Molecular
`weight
`
`Melting puinl
`(‘Cl
`
`Specific
`rolalion
`
`H0
`
`266.3
`
`l
`
`CuH:a01
`
`1:) §§+39 {dioxanel
`
`la] 3‘; +308 I200 mg. in ID ml. dioxanel:
`+115 I200 mg. in I0 rnl. alcohol}.
`
`[cl ‘f;;+76- +83 ilflflmg. in lo mi.
`dioxancl
`
`Absorption
`lTIflX.
`
`23 I. N0. 282. 292. 315. 3-1-1] I‘I']](
`
`28 3-285 my
`
`225. no my
`
`APOTEX_AZFL 0061958
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 15 of 20 PageID #: 1691
`Case 1:14—cv—O1453—LPS Document 48-6 Filed 11/23/15 Page 15 of 20 Page|D #: 1691
`
`STEROID HOIIMONES AND OTHER STEROIIJAL SYNTHETICS (Continued)
`
`‘Narnes&
`synonyms:
`
`ESTRADIOL BENZOATE:
`5-estmiiohi-hen zoame:
`entmdiolmonnhenzoate.
`
`OH
`
`H’:
`
`C23" 230:
`
`Om
`
`316.41
`
`19I-I96
`
`Molecular
`weight
`
`Melting point
`("Cl
`
`Spfggfifion
`Absorption
`[Tl-ii.
`
`ESTRADIOL CYPIONATE;
`esn-adiul czmlopentylprupionate;
`is-estmdiol I‘I—cyc3openIa.nepropiona1e:
`I .J.5( I0}-estrattiene-3. I ‘J3-diol.i ‘I-cyclopentanepropionate.
`
`.
`
`:0
`
`o — _
`("—[CH;);—Cfi
`II
`I
`O
`Hzc
`
`CH2
`‘CH4
`I
`CH3
`
`OH
`
`396.6
`
`|5l—|54
`
`in!) %-I-53— +63 (100 mg. in 10 ml. diuxane)
`
`tu},,+-11,513..‘ Edioxann
`223 my
`
`Names &
`synonyms:
`
`ESTRADIOL DIPROPIONATE:
`afiatmdinl dipropinnalc;
`17,8-cstradiol dipropionale.
`
`ESTRIOL;
`trihydroxarestrin:
`A"'-’- “’-estratIie11&3—l 6-cis-1 ?—
`trans-dfizrl;
`I,3,_'I-cstralrienc-3, l6nI,1 18-trial.
`
`ES'I'RONE;
`folliculln :
`kewhydmmwin:
`r.T.S-eslrxiil-ia'I-3-11%|-7|?’-‘inc.
`
`Cl|l_uCH.-E00
`
`Molecular
`weight
`
`"
`
`334.5
`
`Melting point
`{°C'l
`
`l04—l09
`
`s”f§i:fim
`
`(rs) 2—[:+39 :2 :1 er, in dioxnne}
`
`ta) §+s3 — +63 (40 mg. in I ml. dioxnna)
`
`(11% + Isa — + E63 ll{I).rng_ in 10 ml.
`diunanel
`
`.
`
`l.'l'IHX.
`
`APOTEX_AZFL 0061959
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 16 of 20 PageID #: 1692
`Case 1:14—cv—O1453—LPS Document 48-6 Filed 11/23/15 Page 16 of 20 Page|D #: 1692
`
`STEROID HORMONES AND OTHER STEROIDAL SYNTI-IETICS (Continued)
`
`TRONE IIENZOATE
`
`EIHYNYL ESTRADIOL;
`IT~¢thin3rl asrradiol:
`I‘Ir'o:-ethy11)r1-I,3,5-eslrntricne-3.ITfl-diol.
`
`—
`
`MESTRANOL;
`ethynyipslradiol .‘5—met.hyl ether:
`3-methox;-vl1m-elhynyl-I ,3,S( I0)-
`eslratriene-rI'l'_.'l-cl:
`I'M-ethynyl-estradiol-3-mctliyl cthcr:
`3-mathuxy-I9-nor-ITa-preg:-ra-I .3,5,trien-
`20-yn-I7-0].
`
`Muluculnr
`wei sh!
`
`3?4.4
`
`vc)
`
`Melting Point I‘!-‘I46
`_
`S
`.
`25
`‘I!
`S
`Pfisagon
`{:2} 5+ I20{d1oxaneJ
`ta}1E+I— + 10 (100 mg. :11 ll] ml.
`dioxnnc}
`
`'
`
`310.4
`
`I4B_I5I‘
`{er}
`+2 to +8 (2013 mg.iJ1 I0 ml.
`dioxancl
`
`max.
`
`PROGTOGENS AND PROGESIINS {INCLUDING 19-NORSTERDID COMPOUNDS)
`
`ANAGESTONE ACETATE;
`6:-rficllayl-4-prcanen-11a-ol-20-one
`acetate:
`I?u—aoe1oxy~6u-nmhylpregn-4-ea-10-one;
`I1+:-aoeioxy-6:-methyl-4-pmgrten-20-fine.
`
`CI-ILORMADTNONE ACETATE:
`_6-bhloto-A"-dehylim-17w
`ncetoxyprogesierone;
`6-ci1loroia"‘-pres:md‘:ene-lTu-ol-
`3.10-diorleaoecate.
`
`ACETOXYPREGNENOLONE;
`21-acetoxypngnenolone:
`prebodjolone acxtate:
`A‘-pretawne-3.fl.2l-dial-20-onbll -
`monoaoetatc;
`2l—aoetoxy—5—nresnuw-3-01-2IJ«mc;
`3-hyclmxy-2!-aoetaxy-5-pregrlen-20-one.
`
`"T1-Ia0C0Cll;
`=0
`
`Hac
`
`374.5
`
`I8-$—I85
`
`3?2.I5
`
`112-173
`
`'
`
`2m—2:2
`
`D
`(oz) 213-4 31- +43{dioxaneJ
`
`‘
`
`I
`
`max.
`
`(¢}%+40 to +45 {I0 mg. in 10 ml.
`chloroform]
`
`ta) gins: —6(200m5.in I0 ml.
`chlc-to fonn]
`
`284 my [methanol]
`Log 2 — 4.34 10.02
`
`_
`
`1’ ’
`
`1
`
`APOTEX_AZFL 0061960
`
`

`
`Case 1:14-cv-01453-LPS Document 48-6 Filed 11/23/15 Page 17 of 20 PageID #: 1693
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`
`STEROID HORMONES AND OTHER STEROIDAL SYNTHETICS (Continued)
`
`Dlll-'lEI‘HISTERONE.'.
`6u.,1l -dimcthyiethiswwnc;
`6a,2l -dimellayl-l 75-hydroxy-I Tn:-p:'e1;|1-
`-Hn—21)-yn-3-one:
`6¢-me|l1yI-1T¢-pmpyn;rlandmst-4-¢n-
`I711-o]-3-one:
`I13-hydwxy-6¢-methyl-17¢
`(pm1:»l-ynyl]-androsi-4-one-J-one.
`
`.
`
`ETHI STE RONE:
`anhydrohydroxypmmeslemnse:
`ethinyl testosterone;
`prcmeninolana:
`IT: ethymrl mmosterone:
`|?m-c1hynyi-I7fi-hydroxy-4-
`nndroatcn-3-one.
`
`'ET|-IYNO DIOL DIACETATE;
`l‘.'¢~¢thynyl—4-esuene-SH.lifl-dial-I '.-'-
`dianetalz:
`_
`I9-nor-I7u~prem-4-en-20-yne-313. I 7-dial
`diaceaate.
`
`Molecular
`weight
`
`Meiting point
`(‘C1
`
`S
`
`'
`rotation
`Peclflc
`
`App. I00 tdec.)
`
`266--213
`
`-
`
`.
`.
`ta} % + 16.5 to + l8.5 (2 ‘X. solution :11
`chlmrolhrrn} (calculated to [he
`anhydrous basis}
`
`(ct) 2?: -32° (1021 mg. in_ in m].
`pyridinc)
`
`i26— I 3;‘
`
`'
`'25
`{-11 E~?4 I’! ‘y, in clllorofonut)
`
`fihsorpiion
`max.
`
`Aug. 14-!) mp (anhydn:-us ethanol)
`Ei " cm — -I-i3
`
`24] my [rn-eihanoli
`
`FLUROGESTONE ACETATE:
`1'.-‘:1-acetoxy-9:-fluoro-I I g?-hydmxy-F
`prcanene-3.20-diam.
`
`HYDROXYMET'l-IYl.PF.0-
`GESTERONE;
`medroxypmgestemne:
`I7n:-hydroxyfitm-methylprogesler one;
`I Ta-hydroxydhr-methyl-4-
`pregnene-3.20-dinne.
`
`HYDROXYMETHYLPRG
`GESTERDNE ACETATE:
`medroxyprogesierone acetate;
`I Tn:-hydroxy-Ga-metllylprogesle rone
`acetate;
`I Ta:—hydroxy-6a~metl:yl-4-p1-egnene-
`3,20—diane acetate.
`
`Molecular
`weight
`
`Meltingpoint
`5°C)
`Specific
`rotation
`
`|
`l
`
`Absorption
`max.
`
`250-25:
`
`{: