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Also known as: Medroxyprogesterone 17-acetate, 71-58-9, Provera, Metigestrona, Depo-provera, Farlutin

Molecular Formula

C₂₄H₃₄O₄

Molecular Weight

386.5 g/mol

InChI Key

PSGAAPLEWMOORI-PEINSRQWSA-N

FDA UNII

C2QI4IOI2G

A synthetic progestin that is derived from 17-hydroxyprogesterone. It is a long-acting contraceptive that is effective both orally or by intramuscular injection and has also been used to treat breast and endometrial neoplasms.

1 2D Structure

CAS 71-58-9

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

2.1.2 InChI

InChI=1S/C24H34O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h13-14,18-20H,6-12H2,1-5H3/t14-,18+,19-,20-,22+,23-,24-/m0/s1

2.1.3 InChI Key

PSGAAPLEWMOORI-PEINSRQWSA-N

2.1.4 Canonical SMILES

CC1CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(=O)CC4)C

2.1.5 Isomeric SMILES

C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CC(=O)CC4)C

2.2 Other Identifiers

2.2.1 UNII

C2QI4IOI2G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (6 Alpha)-17-(acetoxy)-6-methylpregn-4-ene-3,20-dione

2. 6 Alpha Methyl 17alpha Hydroxyprogesterone Acetate

3. 6-alpha-methyl-17alpha-hydroxyprogesterone Acetate

4. Curretab

5. Cycrin

6. Depo Medroxyprogesterone Acetate

7. Depo Provera

8. Depo-medroxyprogesterone Acetate

9. Depo-provera

10. Depoprovera

11. Farlutal

12. Gestapuran

13. Medroxyprogesterone 17 Acetate

14. Medroxyprogesterone 17-acetate

15. Medroxyprogesterone 17-acetate, (6 Alpha,17 Alpha)-isomer

16. Medroxyprogesterone 17-acetate, (6 Beta)-isomer

17. Perlutex

18. Pregn-4-ene-3,20-dione, 17-(acetyloxy)-6-methyl-, (6alpha)-

19. Provera

20. Veramix

2.3.2 Depositor-Supplied Synonyms

1. Medroxyprogesterone 17-acetate

2. 71-58-9

3. Provera

4. Metigestrona

5. Depo-provera

6. Farlutin

7. Gestapuran

8. Perlutex

9. Veramix

10. Methylacetoxyprogesterone

11. Amen

12. Medroxyacetate Progesterone

13. Clinovir

14. Depcorlutin

15. Deporone

16. Lutopolar

17. Nadigest

18. Prodasone

19. Progestalfa

20. Progevera

21. Proverone

22. Repromix

23. Sirprogen

24. Supprestral

25. Nidaxin

26. Oragest

27. Depo-promone

28. Promone-e

29. Nsc-26386

30. 6-alpha-methyl-17-alpha-acetoxyprogesterone

31. Cycrin

32. Medroxyprogesteroneacetate

33. Depo-subq Provera 104

34. Depot-medroxyprogesterone Acetate

35. 6-alpha-methyl-17-alpha-hydroxyprogesterone Acetate

36. 17alpha-hydroxy-6alpha-methylprogesterone Acetate

37. 6alpha-methyl-17alpha-hydroxyprogesterone Acetate

38. 6alpha-methyl-4-pregnene-3,20-dion-17alpha-ol Acetate

39. Depot Medroxyprogesterone Acetate

40. Dp150

41. Pregn-4-ene-3,20-dione, 17-(acetyloxy)-6-methyl-, (6alpha)-

42. 17-acetoxy-6alpha-methylprogesterone

43. Aragest

44. Ralovera

45. 6alpha-methyl-17-acetoxy Progesterone

46. Hysron

47. Provera Dosepak

48. Depo-clinovir

49. Depo-ralovera

50. (6alpha)-6-methyl-3,20-dioxopregn-4-en-17-yl Acetate

51. Nsc-21171

52. U 8839

53. C2qi4ioi2g

54. Medroxyprogesterone (acetate)

55. Mls000069442

56. (6alpha)-17-(acetyloxy)-6-methylpreg-4-ene-3,20-dione

57. Chebi:6716

58. Onco-provera

59. Map

60. Medrosterona

61. Clinofem

62. Cykrina

63. Depocon

64. Indivina

65. Mepastat

66. Meprate

67. Repromap

68. Smr000059125

69. Sumiferm

70. Suprestral

71. Tv-46046

72. Veraplex

73. Dugen

74. Pregn-4-ene-3,20-dione, 17-(acetyloxy)-6-methyl-, (6a)-

75. Depo-progestin

76. Depo-prodasone

77. Depo-progevera

78. Perlutex Leo

79. Dsstox_cid_5527

80. Depo-map

81. Aragest 5

82. Med-pro

83. Mpa-beta

84. Dsstox_rid_77819

85. Mpa Hexal

86. Mpa-noury

87. Dsstox_gsid_25527

88. [(6s,8r,9s,10r,13s,14s,17r)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] Acetate

89. Map (steroid)

90. 17alpha-acetoxy-6alpha-methylprogesterone

91. 6alpha-methyl-17alpha-acetoxyprogesterone

92. Depomedroxyprogesterone Acetate

93. Mpa Gym

94. Depo-medroxyprogesterone Acetate

95. Depo-subq Provera

96. Cas-71-58-9

97. Ccris 371

98. 17.alpha.-acetoxy-6.alpha.-methylprogesterone

99. Medroxyprogesterone Acetate [jan]

100. Einecs 200-757-9

101. Unii-c2qi4ioi2g

102. 6alpha-methyl-17-acetoxyprogesterone

103. Nsc 21171

104. Depo-provera Contraceptive

105. 17-acetoxy-6-alpha-methylprogesterone

106. (6.alpha.-pregn-4-ene-3, 17-(acetyloxy)-6-methyl-

107. 17.alpha.-hydroxy-6-.alpha.-methylprogesterone Acetate

108. Pregn-4-ene-3, 17-hydroxy-6.alpha.-methyl-, Acetate

109. 6-alpha-methyl-17-acetoxy Progesterone

110. Brn 2066112

111. Pregn-4-ene-3, 17-(acetyloxy)-6-methyl-, (6.alpha.)-

112. Medroxyprogesterone-17-acetate

113. Ai3-60127

114. Pregn-4-ene-3,20-dione, 17-(acetyloxy)-6-methyl-, (6.alpha.)-

115. 17-acetoxy-6.alpha.-methylprogesterone

116. 6.alpha.-methyl-17-acetoxyprogesterone

117. Ncgc00094713-01

118. 17alpha-hydroxy-6-alpha-methylprogesterone Acetate

119. Progesterone, 17-hydroxy-6alpha-methyl-, Acetate

120. 17-alpha-hydroxy-6-alpha-methylprogesterone Acetate

121. Provera (tn)

122. Depo-provera (tn)

123. 6alpha-methyl-17alpha-acetoxypregn-4-ene-3,20-dione

124. Medroxyprogesterone Acetate [usp:jan]

125. 17-alpha-acetoxy-6-alpha-methylpregn-4-ene-3,20-dione

126. 17alpha-acetoxy-6-alpha-methylpregn-4-ene-3,20-dione

127. 6-alpha-methyl-17-alpha-acetoxypregn-4-ene-3,20-dione

128. Progesterone, 17-alpha-hydroxy-6-alpha-methyl-, Acetate

129. Medroxyprogesterone Acetate [progestins]

130. 6-alpha-methyl-4-pregnene-3,20-dion-17-alpha-ol Acetate

131. 6.alpha.-methyl-17.alpha.-acetoxyprogesterone

132. (6-alpha)-17-(acetyloxy)-6-methylpreg-4-ene-3,20-dione

133. 17alpha-hydroxy-6alpha-methylpregn-4-ene-3,20-dione Acetate

134. 6alpha-pregn-4-ene-3,20-dione, 17-(acetyloxy)-6-methyl-

135. Cpd000653524

136. 17-alpha-hydroxy-6-alpha-methylpregn-4-ene-3,20-dione Acetate

137. Medroxyprogesteroni Acetas

138. Opera_id_1110

139. Medroxyprogesterone-acetate

140. 17.alpha.-hydroxy-6.alpha.-methylprogesterone Acetate

141. 6.alpha.-methyl-17.alpha.-hydroxyprogesterone Acetate

142. Medroxiprogesterone Acetate

143. Chembl717

144. Schembl4276

145. 6.alpha.-methyl-17.alpha.-acetoxypregn-4-ene-3,20-dione

146. 17.alpha.-acetoxy-6-.alpha.-methylpregn-4-ene-3,20-dione

147. 4-08-00-02212 (beilstein Handbook Reference)

148. 6.alpha.-methyl-4-pregnene-3,20-dion-17.alpha.-ol Acetate

149. Mls001148217

150. Mls002207115

151. 17.alpha.-hydroxy-6.alpha.-methylpregn-4-ene-3,20-dione Acetate

152. Depo-subq Provera 104 (tn)

153. Dtxsid0025527

154. Hms2233o07

155. Hms2235e05

156. Hms3259o14

157. Hms3884b10

158. Pregn-4-ene-3,20-dione, 17-hydroxy-6alpha-methyl-, Acetate

159. (6-alpha)-pregn-4-ene-3,20-dione, 17-(acetyloxy)-6-methyl-

160. (6s,8r,9s,10r,13s,14s,17r)-17-acetyl-6,10,13-trimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl Acetate

161. Cbp-1011

162. Hy-b0469

163. Nsc21171

164. Nsc26386

165. Zinc5029557

166. Tox21_111319

167. Tox21_200141

168. Bdbm50067678

169. S2567

170. Akos015894870

171. Tox21_111319_1

172. Ac-2174

173. Ccg-264965

174. Db00603

175. Nc00574

176. Medroxyprogesterone Acetate (jp17/usp)

177. Mrf-0000023

178. Ncgc00022037-03

179. Ncgc00022037-04

180. Ncgc00022037-05

181. Ncgc00022037-07

182. Ncgc00257695-01

183. Ncgc00263480-01

184. As-13981

185. Medroxyprogesterone Acetate [iarc]

186. Smr000653524

187. Medroxyprogesterone Acetate [mart.]

188. Medroxyprogesterone Acetate [vandf]

189. Medroxyprogesterone 17-acetate [mi]

190. Medroxyprogesterone Acetate [usp-rs]

191. Medroxyprogesterone Acetate [who-dd]

192. Medroxyprogesterone Acetate [who-ip]

193. C08150

194. C76275

195. D00951

196. Ab00384270-14

197. Ab00384270_15

198. Medroxyprogesterone 17-acetate, >=97% (hplc)

199. Medroxyprogesterone Acetate [orange Book]

200. Medroxyprogesteroni Acetas [who-ip Latin]

201. 010m483

202. Medroxyprogesterone Acetate [ep Monograph]

203. Medroxyprogesterone Acetate [usp Monograph]

204. Megestrol Acetate Impurity A [ep Impurity]

205. Lunelle Component Medroxyprogesterone Acetate

206. Prempro Component Medroxyprogesterone Acetate

207. Q2823834

208. (6?)-6-methyl-3,20-dioxopregn-4-en-17-yl Acetate

209. 6.alpha.-pregn-4-ene-3, 17-(acetyloxy)-6-methyl-

210. Medroxyprogesterone Acetate Component Of Lunelle

211. Medroxyprogesterone Acetate Component Of Prempro

212. Premphase Component Medroxyprogesterone Acetate

213. Medroxyprogesterone Acetate Component Of Premphase

214. Medroxyprogesterone 17-acetate 100 Microg/ml In Methanol/water

215. Medroxyprogesterone-17-acetate 100 Microg/ml In Acetonitrile

216. 17-hydroxy-6.alpha.-methylpregn-4-ene-3,20-dione Acetate

217. Medroxyprogesterone 17-acetate, Vetranal(tm), Analytical Standard

218. Medroxyprogesterone Acetate, European Pharmacopoeia (ep) Reference Standard

219. Medroxyprogesterone Acetate, Pharmaceutical Secondary Standard; Certified Reference Material

220. Medroxyprogesterone Acetate, United States Pharmacopeia (usp) Reference Standard

221. Medroxyprogesterone Acetate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

222. Medroxyprogesterone Acetate For System Suitability, European Pharmacopoeia (ep) Reference Standard

223. Medroxyprogesterone Acetate, For Performance Test, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₄O₄
Molecular Weight	386.5 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	386.24570956 g/mol
Monoisotopic Mass	386.24570956 g/mol
Topological Polar Surface Area	60.4 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	767
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	DEPO-PROVERA
Active Ingredient	MEDROXYPROGESTERONE ACETATE
Company	PHARMACIA AND UPJOHN (Application Number: N012541); PHARMACIA AND UPJOHN (Application Number: N020246)

2 of 6
Drug Name	DEPO-SUBQ PROVERA 104
Active Ingredient	MEDROXYPROGESTERONE ACETATE
Company	PHARMACIA AND UPJOHN (Application Number: N021583. Patent: 6495534)

3 of 6
Drug Name	MEDROXYPROGESTERONE ACETATE
Active Ingredient	MEDROXYPROGESTERONE ACETATE
Company	AMPHASTAR PHARMS INC (Application Number: A077235); AMPHASTAR PHARMS INC (Application Number: A077334); BARR (Application Number: A040159); TEVA PHARMS USA (Application Number: A076553)

4 of 6
Drug Name	PROVERA
Active Ingredient	MEDROXYPROGESTERONE ACETATE
Company	PHARMACIA AND UPJOHN (Application Number: N011839)

5 of 6
Drug Name	PREMPHASE 14/14
Active Ingredient	ESTROGENS, CONJUGATED; MEDROXYPROGESTERONE ACETATE
Company	WYETH PHARMS INC (Application Number: N020527)

6 of 6
Drug Name	PREMPRO
Active Ingredient	ESTROGENS, CONJUGATED; MEDROXYPROGESTERONE ACETATE
Company	WYETH PHARMS INC (Application Number: N020527)

4.2 Drug Indication

Medroxyprogesterone acetate (MPA) oral tablets are indicated to treat secondary amenorrhea, reduce the incidence of endometrial hyperplasia in postmenopausal women, and to treat abnormal uterine bleeding due to hormonal imbalance, not organic pathology. Oral tablets containing MPA and conjugated estrogens are indicated to prevent postmenopausal osteoporosis and to treat moderate to severe menopausal symptoms such as vasomotor symptoms, vulvar atrophy, and vaginal atrophy. Subcutaneous MPA is indicated to prevent pregnancy and manage pain associated with endometriosis. Intramuscular MPA is indicated to prevent pregnancy, and at higher concentrations for palliative treatment of endometrial or renal carcinoma.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Medroxyprogesterone acetate (MPA) inhibits gonadotropin production, reduces nuclear estrogen receptors and DNA synthesis in epithelial cells of the endometrium, and induces p53 dependant apoptosis in cancer cell lines. MPA oral tablets have a half life of 40-60 hours and other formulations can have half lives that are considerably longer, so the duration of action is long. The therapeutic window is wide as patients may take doses ranging from 5mg orally daily to 1000mg as a depo injection weekly. Long term use of MPA is associated with a reduction in bone density and patients who taking MPA during adolescence may have lower peak bone mass than untreated patients, which can also increase the risk of osteoporosis and fractures in the future.

5.2 MeSH Pharmacological Classification

Contraceptive Agents, Female

Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)

Contraceptive Agents, Male

Chemical substances or agents with contraceptive activity in males. Use for male contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Male.)

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

Contraceptive Agents, Hormonal

Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Progestin [EPC]; Progesterone Congeners [CS]

5.4 Absorption, Distribution and Excretion

Absorption

Absorption of oral medroxyprogesterone acetate (MPA) varies considerably between formulations. A 1000mg oral dose reaches an average C_max of 145-315nmol/L while a 500mg oral dose reaches an average C_max of 33-178nmol/L with a T_max of 1-3 hours and a lag time of half an hour. The AUC of a 500mg oral dose of MPA was 543.4-1981.1nmol\*L/h depending on formulation. Intramuscular MPA reaches a C_max of 4.691.52nmol/L with a T_max of 4.752.09 days and an AUC of 81.5827.64days\*nmol/L. Subcutaneous MPA reaches a C_max of 3.831.56nmol/L with a Tmax of 6.522.07 days and an AUC of 72.2638.73days\*nmol/L. However, the pharmacokinetics of MPA may also vary depending on injection site.

Route of Elimination

The majority of medroxyprogesterone acetate (MPA) is eliminated in the urine as glucuronide conjugates and a minority of sulphate conjugates. Glucuronide conjugates are also detected in the feces. Determining the exact ratio of metabolites and parent compound eliminated in the urine and feces is difficult as the metabolite profile in the urine is not significantly different and radio labelling studies are not readily available.

Volume of Distribution

The volume of distribution of medroxyprogesterone acetate is 203L.

Clearance

The mean clearance of medroxyprogesterone acetate (MPA) is 1668146L/day or 21.94.3L/kg/day. Due to the high inter patient variability in MPA pharmacokinetics, clearance has been reported to be 1600-4000L/day.

5.5 Metabolism/Metabolites

Medroxyprogesterone acetate undergoes beta hydroxylation to form the metabolites 6-beta (M-2), 2-beta (M-4), and 1-beta-hydroxymedroxyprogesterone acetate (M-3). M-2 and M-4 are further metabolized to 2-beta,6-beta-dihydroxymedroxyprogesterone (M-1). M-3 is further metabolized to 1,2-dehydromedroxyprogesterone acetate (M-5).

Medroxyprogesterone Acetate has known human metabolites that include M-2, M-3, and Medroxyprogesterone Acetate.

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

5.6 Biological Half-Life

Oral medroxyprogesterone acetate (MPA) has an absorption half life of 15-30min and a biological half life of 40-60 hours. Intramuscular MPA has an absorption half life of 0.860.30 days and an elimination half life of 24.0321.74 days. Subcutaneous MPA has an absorption half life of 1.050.56 days and an elimination half life of 30.9015.11 days.

5.7 Mechanism of Action

Medroxyprogesterone acetate (MPA) inhibits the production of gonadotropin, preventing follicular maturation and ovulation, which is responsible for its ability to prevent pregnancy. This action also thins the endometrium. MPA reduces nuclear estrogen receptors and DNA synthesis in epithelial cells of the endometrium. MPA can also induce p53 dependant apoptosis in certain cancer cell lines, and inhibit GABA-A receptors.

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