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17 Hydroxyprogesterone
Also known as: 17alpha-hydroxyprogesterone, 68-96-2, 17-hydroxyprogesterone, 17a-hydroxyprogesterone, Prodix, Prodox
Molecular Formula
C21H30O3
Molecular Weight
330.5  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.
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 MeSH Synonyms

1. 17 Alpha Hydroxyprogesterone

2. 17 Alpha-hydroxyprogesterone

3. 17 Hydroxyprogesterone

4. 17-alpha-hydroxyprogesterone

5. 17-hydroxyprogesterone

6. 17-hydroxyprogesterone, (17 Alpha)-isomer

7. 17-hydroxyprogesterone, (9 Beta, 10 Alpha)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 17alpha-hydroxyprogesterone

2. 68-96-2

3. 17-hydroxyprogesterone

4. 17a-hydroxyprogesterone

5. Prodix

6. Prodox

7. Gestageno Gador

8. 17-alpha-hydroxyprogesterone

9. 17-hydroxypregn-4-ene-3,20-dione

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

11. Setaderm

12. Oxiprogesteronum

13. 17alpha-hydroxy-progesterone

14. 17alpha-hydroxy-4-pregnene-3,20-dione

15. Hidroxiprogesterona

16. Hydroxyprogesteronum

17. Pregn-4-ene-3,20-dione-17-ol

18. Gestageno

19. Idrossiprogesterone [dcit]

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

21. 17

22. A-hydroxyprogesterone

23. Hydroxyprogesteronum [inn-latin]

24. Hidroxiprogesterona [inn-spanish]

25. 17-oh Progesterone

26. 17-hydroxypregn-4-en-3,20-dione

27. 17.alpha.-hydroxyprogesterone

28. Hsdb 3343

29. 604-09-1

30. Chebi:17252

31. Nsc-15468

32. Mls000028453

33. 17-ohp

34. (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

35. 4-pregnen-17a-ol-3,20-dione

36. U 3096

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

38. 4-pregnen-17alpha-ol-3,20-dione

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

40. Ncgc00093949-03

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

42. Smr000058349

43. 21807m87j2

44. Hydroxyprogesterone (inn)

45. (9beta)-17-hydroxypregn-4-ene-3,20-dione

46. U-3096

47. Dsstox_cid_20747

48. Dsstox_rid_79586

49. Dsstox_gsid_40747

50. Hydroxyprogesterone [inn]

51. Alpha Hydroxy Progesterone

52. Idrossiprogesterone

53. Cas-68-96-2

54. 17ohp

55. Hydroxyprogesterone [inn:ban]

56. Einecs 200-699-4

57. Nsc 15468

58. 17alpha Hydroxyprogesterone

59. Brn 2062088

60. Mfcd00003659

61. Unii-21807m87j2

62. 3qz

63. 17a-hydroxypregn-4-ene-3,20-dione

64. 17-hydroxy-progesterone

65. 17-a-hydroxyprogesterone

66. Opera_id_1812

67. 17?-hydroxy Progesterone

68. Bmse000472

69. Bmse000598

70. Epitope Id:152220

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. Gtpl5104

80. Progesterone, 17alpha-hydroxy-

81. Dtxsid6040747

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

83. Pregn-4-ene-3, 17-hydroxy-

84. Dtxsid00859075

85. Hydroxyprogesterone [hsdb]

86. Hms2090m08

87. Hms2234j04

88. Hms3261b12

89. Hydroxyprogesterone [vandf]

90. D4-pregnen-17a-ol-3,20-dione

91. Hy-b0891

92. Nsc15468

93. Pregn-4-en-17a-ol-3,20-dione

94. Zinc5434436

95. Hydroxyprogesterone [who-dd]

96. Tox21_111233

97. Tox21_301530

98. Tox21_500565

99. Bdbm50423511

100. Lmst02030161

101. S4507

102. 17alpha-hydroxyprogesterone, >=95%

103. Akos015955623

104. Tox21_111233_1

105. Ccg-204655

106. Cs-4354

107. Db14570

108. Fd12004

109. Ks-5312

110. Lp00565

111. Sdccgsbi-0050548.p002

112. 4-pregnen-17.alpha.-ol-3,20-dione

113. Ncgc00093949-04

114. Ncgc00093949-05

115. Ncgc00093949-08

116. Ncgc00255425-01

117. Ncgc00261250-01

118. 17alpha-hydroxy-pregn-4-ene-3,20-dione

119. 17.alpha.-hydroxyprogesterone [mi]

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

121. Eu-0100565

122. H1250

123. C01176

124. D08052

125. H 5752

126. 17-hydroxypregn-4-ene-3,20-dione, (+/-)-

127. Ab00490003-08

128. Q175901

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

130. W-104646

131. 17-hydroxypregn-4-ene-3,20-dione-, (17.alpha.)-

132. 7a45bef6-add0-4b3e-a014-2de930d3b67b

133. 17-alpha-hydroxyprogesterone 100 Microg/ml In Methanol

134. 17alpha-hydroxyprogesterone, Vetranal(tm), Analytical Standard

135. (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

136. (8r,10r,13s,17r)-17-acetyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

137. (8r,9s,10r,13s,14s,17r)-17-acetyl-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one

138. 110850-01-6

139. 17alpha-hydroxyprogesterone Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 330.5 g/mol
Molecular Formula C21H30O3
XLogP33.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass330.21949481 g/mol
Monoisotopic Mass330.21949481 g/mol
Topological Polar Surface Area54.4 Ų
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


For more Therapeutic Uses (Complete) data for 17ALPHA-HYDROXYPROGESTERONE (15 total), please visit the HSDB record page.


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 FDA Pharmacological Classification
5.1.1 Active Moiety
HYDROXYPROGESTERONE
5.1.2 FDA UNII
21807M87J2
5.1.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Progestin
5.2 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


5.3 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


5.4 Metabolism/Metabolites

17alpha-hydroxy-progesterone has known human metabolites that include 17Beta-21-dihydroxyprogesterone.

17alpha-hydroxy-progesterone is a known human metabolite of progesterone.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


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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Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Ste...
Symbiotec, a leading API manufacturing company based in Indore, Central India, specializes in Cortico-Steroids and Steroid-Hormone APIs. Since 1995, their focus on R&D, sustainable operations, and innovation has driven their commitment to improving global healthcare access. With a state-of-the-art manufacturing facility inaugurated in 2004, Symbiotec has become a trusted provider in the industry. Their certifications including WHO-GMP, ISO, US FDA, and EU GMP showcase their dedication to quality and excellence. Over two decades, they've maintained their position through adaptability, efficiency, and competitive pricing.
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With the high technology and excellent services, Xianju pharma earned a top worldwide reputation for quality in pharmaceutical industry. Xianju pharma has dedicated to scientific research since we were established in 1972.We developed over 100 Active Pharmaceutical Ingredients and finished formulations from then on , becoming a leader of steroids and hormones manufacturing in China. Xianju pharma has full of confidence to be a global supplier of active pharmaceutical ingredients with customized solid state specifications and unparalleled intellectual property that accomplishment our cooperation.
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