(1S,2R,8S,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl acetate

• ChemBase ID: 73209
• Molecular Formular: C24H34O4
• Molecular Mass: 386.52436
• Monoisotopic Mass: 386.24570957
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](C[C@@H]2C)[C@H]2[C@](CC1)([C@](CC2)(C(=O)C)OC(=O)C)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(OC(=O)C)C(=O)C)C)C
• 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
• InChIKey: PSGAAPLEWMOORI-PEINSRQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl acetate; (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: provera; (1S,2R,8S,10R,11S,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: (6α)-17-(Acetyloxy)-6-methyl-pregn-4-ene-3,20-dione; 17α-Acetoxy-6α-methylpregn-4-ene-3,20-dione; 17α-Hydroxy-6α-methylprogesterone Acetate; Meprate; Metigestrona; NSC 21171; NSC 26386; Nadigest; Nidaxin; Novo-Medrone; Oragest; Perlutex; Perlutex Leo; Prodasone; Progespon; Progestalfa; Progeston; Progevera; Provera; Proverone; Ralovera; Repromap; Repromix; Sirprogen; Sodelut G; U 8839; Veramix; Medroxy Progesterone 17-Acetate; Medroxyprogesterone 17-acetate; MPA; Medroxyprogesterone acetate; Medroxyprogesterone 17-acetate; 17α-Acetoxy-6α-methylprogesterone; 17α-Hydroxy-6α-methyl-4-pregnene-3,20-dione 17-acetate; 6α-Methyl-17α-acetoxyprogesterone; 6α-Methyl-17α-hydroxyprogesterone acetate; Medroxyprogesone acetate; 17α-乙酰氧基-6α-甲基孕酮; 17α-羟基-6α-甲基-4-孕烯-3,20-二酮 17-乙酸酯; 6α-甲基-17α-乙酰氧孕酮; 6α-甲基-17α-羟基孕酮乙酸酯; 醋酸甲羟孕酮

Database IDs

• CAS Number: 71-58-9
• EC Number: 200-757-9
• MDL Number: MFCD00010483
• Beilstein Number: 2066112
• PubChem SID: 24870140; 162038129; 24896674
• PubChem CID: 6279

CALCULATED PROPERTIES

• Acid pKa: 17.821218
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.129324
• LogD (pH = 7.4): 4.129324
• Log P: 4.129324
• Molar Refractivity: 107.8054 cm^3
• Polarizability: 42.687153 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 206-207 °C(lit.); 206-208°C
• Optical Rotation: [α]25/D +58°, c = 1 in chloroform

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: TU5010000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40-48
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Gene Information: human ... AR(367), ESR1(2099), ESRRA(2101), NR3C1(2908), NR3C2(4306), PGR(5241)rat ... Ar(24208)
• Mechanism of Action: Gonadotropin secretion inhibitor; Progestogen

Product Information

• Purity: ≥97% (HPLC); 97%
• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Used as an injectable contraceptive
• Empirical Formula (Hill Notation): C24H34O4

DETAILS

Selleck Chemicals - S2567

Research Area: Cancer
Biological Activity:
Medroxyprogesterone acetate is a progestin, a synthetic variant of the human hormone progesterone and a potent progesterone receptor agonist. Medroxyprogesterone acetate is used as a contraceptive, in hormone replacement therapy and for the treatment of endometriosis as well as several other indications. Medroxyprogesterone acetate is a more potent derivative of its parent alcohol medroxyprogesterone. While medroxyprogesterone is sometimes used as a synonym for medroxyprogesterone acetate ), what is normally being administered is medroxyprogesterone 17-acetate and not medroxyprogesterone. Medroxyprogesterone acetate has approximately 100 fold higher binding affinity and transactivation potency compared to medroxyprogesterone. [1][2]

Sigma Aldrich - M1629

Biochem/physiol Actions
Medroxyprogesterone 17-acetate (MPA) is a synthetic progestin used as a contraceptive, in hormone replacement therapy and for the treatment of endometriosis. It is a more potent progestin that the nonacetylated form.

Sigma Aldrich - 46412

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M203560

Progestogen; an injectable contraceptive.

REFERENCES

• Lenco W et al. Ann Surg. 1975 Jan;181(1):67-73.
• Tang, M., et al.: Endocrinol., 151, 1320 (2010)
• Lee, K., et al.: Mol. Cell. Endocrinol., 319, 109 (2010)
• Rodgers, A., et al.: Chem., Res. Toxicol., 23, 724 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)