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17-Hydroxyprogesterone
PharmaCompass
17-Hydroxyprogesterone
Also known as: 17alpha-hydroxyprogesterone, 17-hydroxyprogesterone, 68-96-2, 17a-hydroxyprogesterone, Prodix, Prodox
Molecular Formula
C21H30O3
Molecular Weight
330.468  g/mol
InChI Key
DBPWSSGDRRHUNT-CEGNMAFCSA-N
FDA UNII
21807M87J2

A metabolite of PROGESTERONE with a hydroxyl group at the 17-alpha position. It serves as an intermediate in the biosynthesis of HYDROCORTISONE and GONADAL STEROID HORMONES.
Hydroxyprogesterone is a Progestin. The chemical classification of hydroxyprogesterone is Progesterone Congeners.
1 2D Structure

17-Hydroxyprogesterone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
2.1.2 InChI
InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
2.1.3 InChI Key
DBPWSSGDRRHUNT-CEGNMAFCSA-N
2.1.4 Canonical SMILES
CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
2.1.5 Isomeric SMILES
CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
2.2 Other Identifiers
2.2.1 UNII
21807M87J2
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 17alpha-hydroxyprogesterone

2. 17-hydroxyprogesterone

3. 68-96-2

4. 17a-hydroxyprogesterone

5. Prodix

6. Prodox

7. Gestageno Gador

8. Setaderm

9. Oxiprogesteronum

10. 17-hydroxypregn-4-ene-3,20-dione

11. 17alpha-hydroxy-4-pregnene-3,20-dione

12. 17-alpha-hydroxyprogesterone

13. 17alpha-hydroxy-progesterone

14. Hidroxiprogesterona

15. Hydroxyprogesteronum

16. Pregn-4-ene-3,20-dione, 17-hydroxy-

17. Gestageno

18. Idrossiprogesterone [dcit]

19. Pregn-4-ene-3,20-dione-17-ol

20. Delta(4)-pregnene-17alpha-ol-3,20-dione

21. Hydroxyprogesteronum [inn-latin]

22. Hidroxiprogesterona [inn-spanish]

23. 17-oh Progesterone

24. Hsdb 3343

25. 17-hydroxypregn-4-en-3,20-dione

26. Hydroxyprogesterone [inn:ban]

27. Chebi:17252

28. Unii-21807m87j2

29. Einecs 200-699-4

30. Nsc 15468

31. 17alpha Hydroxyprogesterone

32. Brn 2062088

33. 17ohp

34. 17.alpha.-hydroxyprogesterone

35. Mls000028453

36. 4-pregnen-17a-ol-3,20-dione

37. Dbpwssgdrrhunt-cegnmafcsa-n

38. U 3096

39. 4-pregnen-17alpha-ol-3,20-dione

40. (8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one

41. 604-09-1

42. Delta4-pregnen-17alpha-ol-3,20-dione

43. Ncgc00093949-03

44. Ak103604

45. Alpha-17hydroxypregn-4-ene-3,20-dione

46. Smr000058349

47. Dsstox_cid_20747

48. Dsstox_rid_79586

49. Dsstox_gsid_40747

50. Pregn-4-ene-3,20-dione, 17-hydroxy-, (17a)-

51. Alpha Hydroxy Progesterone

52. Idrossiprogesterone

53. Cas-68-96-2

54. 17alpha-hydroxypregn-4-ene-3,20-dione

55. (9beta)-17-hydroxypregn-4-ene-3,20-dione

56. Hydroxyprogesterone;

57. 3qz

58. 17-alpha-hydroxypregn-4-ene-3,20-dione

59. 17-hydroxyprogeoterone

60. 17-hydroxy-progesterone

61. 17-a-hydroxyprogesterone

62. Opera_id_1812

63. 17

64. A-hydroxyprogesterone

65. Hydroxyprogesterone (inn)

66. Bmse000472

67. Bmse000598

68. D06wbh

69. Epitope Id:152220

70. Ac1l1m3c

71. Schembl8068

72. Chembl1062

73. Bidd:pxr0103

74. Lopac0_000565

75. 17.alpha.-hydoxyprogesterone

76. 4-08-00-02189 (beilstein Handbook Reference)

77. Mls001076300

78. Mls002695950

79. 17-ohp

80. Gtpl5104

81. Progesterone, 17alpha-hydroxy-

82. Dtxsid6040747

83. Pregn-4-ene-3,20-dione, 17-hydroxy-, (17.alpha.)-

84. 17

85. A-oc>>u>>aeiai Feminine

86. Ctk8f3204

87. Pregn-4-ene-3, 17-hydroxy-

88. Molport-002-507-146

89. Bb_nc-0621

90. Hms2090m08

91. Hms2234j04

92. Hms3261b12

93. D4-pregnen-17a-ol-3,20-dione

94. Ebd34989

95. Hy-b0891

96. Nsc15468

97. Pregn-4-en-17a-ol-3,20-dione

98. Zinc5434436

99. Tox21_111233

100. Tox21_301530

101. Tox21_500565

102. Abp000341

103. Bdbm50423511

104. Ch0032

105. Lmst02030161

106. Nsc-15468

107. S4507

108. 17alpha-hydroxyprogesterone, >=95%

109. 17a-hydroxypregn-4-ene-3,20-dione

110. Akos015955623

111. Tox21_111233_1

112. Acn-031972

113. Ccg-204655

114. Cs-4354

115. Ks-5312

116. Lp00565

117. Mcule-1412596642

118. 4-pregnen-17.alpha.-ol-3,20-dione

119. Ncgc00093949-04

120. Ncgc00093949-05

121. Ncgc00255425-01

122. Ncgc00261250-01

123. Aj-54084

124. An-41913

125. Cc-03833

126. H581

127. Pl001311

128. Sc-46850

129. 17alpha-hydroxy-pregn-4-ene-3,20-dione

130. Ls-118696

131. 17.alpha.-hydroxypregna-4-ene-3,20-dione

132. 21807m87j2

133. Eu-0100565

134. St24021390

135. St50411345

136. V1408

137. C01176

138. D08052

139. H 5752

140. 92478-ep2295416a2

141. 92478-ep2295426a1

142. 92478-ep2295427a1

143. 92478-ep2298748a2

144. 92478-ep2305642a2

145. Ab00490003-08

146. C-20028

147. W-104646

148. 17-hydroxypregn-4-ene-3,20-dione-, (17.alpha.)-

149. 7a45bef6-add0-4b3e-a014-2de930d3b67b

150. 17alpha-hydroxyprogesterone, Vetranal(tm), Analytical Standard

151. 17

152. A-oc>>uoethcthorn-4-i(c)-3,20- Paragraph Signthorni Feminine

153. (1s,11s,15s,2r,10r,14r)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7 .0.0<2,7>.0<11,15>]heptadec-6-ene

154. (1s,2r,10r,11s,14r,15s)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0(2),?.0(1)(1),(1)?]heptadec-6-en-5-one

155. (1s,2r,10r,11s,14r,15s)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

156. 1050677-68-3

157. 17alpha-hydroxyprogesterone Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

158. 67085-08-9

159. Hydroxyprogesterone / 17a-hydroxyprogesterone; 4-pregnen-17a-ol-3,20-dione; 17a-hydroxypregn-4-ene-3,20-dione

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 330.468 g/mol
Molecular Formula C21H30O3
XLogP33.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass330.219 g/mol
Monoisotopic Mass330.219 g/mol
Topological Polar Surface Area54.4 A^2
Heavy Atom Count24
Formal Charge0
Complexity635
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

THERAPEUTIC USES. ...CONTRACEPTION...FUNCTIONAL UTERINE BLEEDING... DYSMENORRHEA...PREMENSTRUAL TENSION...ENDOMETRIOSIS...THREATENED & HABITUAL ABORTION...EVALUATION OF OVARIAN FUNCTION & DIAGNOSIS OF PREGNANCY...SUPPRESSION OF POST-PARTUM LACTATION...ENDOMETRIAL CARCINOMA. /PROGESTINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1439


CHEMOTHERAPEUTIC AGENTS USEFUL IN NEOPLASTIC DISEASE: HYDROXYPROGESTERONE CAPROATE (DELALUTIN) FOR ENDOMETRIUM, RENAL CELL, BREAST, PROSTATE. /CAPROATE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1251


...IN METASTATIC & RECURRENT ENDOMETRIAL CARCINOMA. THEY PRODUCE REMISSIONS FOR PROLONGED PERIODS IN ABOUT 25% OF PT WHEN METASTASES ARE CONFINED TO PULMONARY AREA. LARGER DOSES...WHEN DISEASE RECURS IN OSSEOUS, INTRA-ABDOMINAL, OR PELVIC SITES. ...USED PARENTERALLY IN RENAL CARCINOMA. /PROGESTAGEUS/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 1142


WHEN USED TO REGULATE IRREGULAR ESTRUS CYCLE, IT IS USUALLY COMBINED WITH ESTROGEN. /CAPROATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 922


THIS COMPD IS USED MAINLY TO CONTROL DYSFUNCTIONAL UTERINE BLEEDING, & ALSO FOR THREATENED & HABITUAL ABORTIONS & PREMATURE LABOR. /CAPROATE/

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 870


POSSESSES ACTIONS & USES OF PROGESTINS, EXCEPT THAT IT DOES NOT PREVENT OVULATION. /CAPROATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 922


PROGESTIN ALONE HAS COME TO BE CALLED "MINIPILLS"... "MINIPILL" WERE INTRODUCED IN ORDER TO ELIMINATE ESTROGEN, AGENT...THOUGHT TO BE RESPONSIBLE FOR MOST IF NOT ALL OF...SIDE EFFECTS OF ORAL CONTRACEPTIVES. ...EFFICACY OF "MINIPILL" HAS BEEN ABOUT 97-98%...& MENSTRUAL CYCLES ARE MORE IRREGULAR. /PROGESTINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1442


IN SEXUAL INFANTILISM IN FEMALE, PROGESTINS MAY BE COMBINED WITH ESTROGENS TO BRING ABOUT GENITAL DEVELOPMENT & MATURATION. PROGESTINS MAY DECR BREAST SIZE IN MASTODYNIA. /PROGESTINS/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 921


PROGESTINS MAY BE USED CYCLICALLY IN TREATMENT OF INFERTILITY IN WHICH UTERUS IS NOT RECEPTIVE TO IMPLANTATION... THEY MAY ALSO BE USED TO LESSEN PREMENSTRUAL TENSION... /PROGESTINS/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 921


IN PREECLAMPSIA & TOXEMIA OF PREGNANCY DUE TO HORMONAL IMBALANCE, PROGESTINS PLUS ESTROGENS MAY IMPROVE CONDITION, EVEN THOUGH BOTH TYPES OF HORMONE CAN CAUSE SALT & WATER RETENTION... /PROGESTINS/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 921


IT IS QUITE ACTIVE BY ORAL ROUTE... ACETATE IS PRESENTLY ONLY ADMIN ORALLY BUT IT IS ALSO ACTIVE BY PARENTERAL ROUTES. ACETATE HAS BEEN REPLACED LARGELY BY CAPROATE... /ACETATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 925


...ACETIC ACID ESTER...APPRECIABLE ACTIVITY & COULD BE TAKEN BY MOUTH, ALTHOUGH VERY LARGE DOSES...REQUIRED. ...GIVEN BY INJECTION IN OIL, ACTIVITY WAS PROLONGED, PROPERTY SHARED BY OTHER ESTERS SUCH AS VALERATE & CAPROATE. CAPROATE...USED EXTENSIVELY AS LONG-ACTING PROGESTIN...INACTIVE BY MOUTH. /ESTER, VALERATE, CAPROATE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1436


VET: ORALLY, IN BITCHES TO INHIBIT ESTRUS, REGRESS MAMMARY TUMORS IN BITCHES WITH FREQUENT, IRREGULAR, OR PROLONGED ESTRUS, & TO TERMINATE PSEUDOPREGNANCY.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 269


VET: ...ITS EFFECTS ARE THOSE OF PROGESTERONE, HELPING TO PRODUCE OR MAINTAIN UTERINE ENDOMETRIUM IN PHYSIOLOGIC STATE CHARACTERISTIC OF PREGNANCY.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 269


IM TREATMENT OF COWS WITH OVARIAN FOLLICULAR CYSTS WITH LUTEUM-DEPOT (CONTAINIG 100 MG 17ALPHA-HYDROXYPROGESTERONE CAPROATE & 10 MG PROGESTERONE) CAUSED LUTEINIZATION OF CYSTS WITHIN 10 DAYS IN 50% & ALL OF THESE COWS SUBSEQUENTLY CONCEIVED.

NAKAO T ET AL; CORNELL VET 68 (2): 161 (1978)


4.2 Drug Warning

VET: AVOID BREEDING TREATED ANIMALS UNTIL SECOND POST-TREATMENT ESTRUS CYCLE. SEVERE PYOMETRA-LIKE SYNDROMES HAVE OCCURRED IN TREATED ANIMALS DEPRIVED OF NORMAL ESTRUS STIMULATING EFFECTS ON UTERINE ENDOMETRIUM...

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 269


WHETHER TAKING ORAL CONTRACEPTIVES OF PROGESTIN-ESTROGEN TYPE PRODUCED HIGHER INCIDENCE OF OCULAR & OPHTHALMO-NEUROLOGIC DISEASES THAN WOULD OCCUR SPONTANEOUSLY IN UNMEDICATED WOMEN OR IN PREGNANT WOMEN WAS NOT ANSWERED CONCLUSIVELY... /PROGESTINS/

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 307


CONTRAINDICATIONS TO THEIR USE ARE THROMBOEMBOLIC DISORDERS OR PAST HISTORY OF THESE CONDITIONS, MARKEDLY IMPAIRED HEPATIC FUNCTION, KNOWN OR SUSPECTED CARCINOMA OF BREAST OR OTHER ESTROGEN-DEPENDENT NEOPLASIA, & UNDIAGNOSED GENITAL BLEEDING. /ORAL CONTRACEPTIVES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1447


5 Pharmacology and Biochemistry
5.1 Pharmacology

Hydroxyprogesterone is a physiological progestin that is produced during glucocorticoid and steroid hormone synthesis and is increased during the third trimester of pregnancy. Hydroxyprogesterone binds to the cytoplasmic progesterone receptors in the reproductive system and subsequently activates progesterone receptor mediated gene expression.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety

HYDROXYPROGESTERONE


5.2.2 FDA UNII

21807M87J2


5.2.3 Pharmacological Classes

Chemical/Ingredient structural concept [Chemical/Ingredient]

Progesterone Congeners


Established Pharmacologic Class [EPC]

Progestin


5.3 ATC Code

G - Genito urinary system and sex hormones
G03 - Sex hormones and modulators of the genital system
G03D - Progestogens
G03DA - Pregnen (4) derivatives
G03DA03 - Hydroxyprogesterone


5.4 Absorption, Distribution and Excretion

...DURATION OF ACTION IS LONGER /THAN PROGESTERONE/, BUT ITS ONSET OF ACTION IS SLOWER. SINGLE INJECTION OF SOLN OF HYDROXYPROGESTERONE CAPROATE IN OIL WILL EXERT PROGESTATIONAL EFFECTS FOR 1-2 WK. /CAPROATE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 922


ABOUT 50-60% OF ADMIN RADIOACTIVE PROGESTERONE APPEARS IN URINE & ABOUT 10% IN FECES. ... WHEN PROGESTERONE IS GIVEN FOR PROLONGED PERIOD, DURING LUTEAL PHASE OF CYCLE, OR DURING PREGNANCY, LARGER PROPORTION (25-30%) APPEARS IN URINE AS PREGUANEDIOL. /PROGESTERONE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1439


RATE OF TURNOVER OF ENDOGENOUS PROGESTERONE IS UNUSUALLY RAPID, T/2 IN BLOOD BEING FEW MIN, & DOUBTLESS EXOGENOUS MATERIAL IS HANDLED IN SAME WAY. SMALL AMT...IS STORED IN BODY FAT... PRESUMABLY, ABSORPTION FROM INTESTINAL TRACT IS PROMPT, BUT COMPD IS RAPIDLY TRANSFORMED DURING PASSAGE THROUGH LIVER... /PROGESTERONE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1439


5.5 Mechanism of Action

ADMIN OF ESTROGEN & PROGESTIN, AS CONTAINED IN COMBINATION OR SEQUENTIAL PREPN, COULD INTERFERE WITH FERTILITY IN ANY ONE OF SEVERAL WAYS. HOWEVER, IT IS CLEAR THAT, AS CURRENTLY USED, MIXTURE INHIBITS OVULATION. ...CONTINUED ACTION OF PROGESTERONE SERVES TO INHIBIT RELEASE OF LH. /PROGESTINS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1443


IT ACTS AS ANTIGONADOTROPHIC AGENT ON ANTERIOR PITUITARY INHIBITING FSH RELEASE &, THUS, FOLLICULAR GROWTH, ESTROGEN PRODUCTION, & ESTRUS. IT ALSO INHIBITS LH RELEASE, THUS PREVENTING OVULATION, CORPORA LUTEA FORMATION, & FURTHER PROGESTERONE SECRETION. BY INHIBITING LH...HOLDS PROGESTERONE LEVELS IN CHECK.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 269


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