Centchroman

Title: Centchroman
CAS Registry Number: 31477-60-8
CAS Name: rel-1-[2-[4-[(3R,4R)-3,4-Dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2H-1-benzopyran-4-yl]phenoxy]ethyl]pyrrolidine
Additional Names: (trans)-1-[2-[p-(7-methoxy-2,2-dimethyl-3-phenyl-4-chromanyl)phenoxy]ethyl]pyrrolidine; 3,4-trans-2,2-dimethyl-3-phenyl-4-[p-(b-pyrrolidinoethoxy)phenyl]-7-methoxychroman; trans-centchroman; ormeloxifene
Trademarks: Centron (Torrent); Saheli (Hindustan Latex)
Molecular Formula: C30H35NO3
Molecular Weight: 457.60
Percent Composition: C 78.74%, H 7.71%, N 3.06%, O 10.49%
Literature References: Estrogen antagonist; synthetic nonsteroidal postcoital antifertility agent. Pharmacology: V. P. Kamboj et al., Indian J. Exp. Biol. 9, 103 (1971); idem et al., ibid. 15, 1144 (1977). Prepd (not claimed): J. W. Bolger, DE 2329201 (1974 to Riker); idem, US 3822287 (1974 to Rexall); S. Ray et al., J. Med. Chem. 19, 276 (1976). Mechanism of action: M. S. Sankaran, M. R. N. Prasad, Contraception 9, 279 (1974). Clinical pharmacology: R. Vaidya et al., ibid. 1173. Physicochemical properties: R. K. Seth et al., Indian J. Pharm. Sci. 45, 14 (1983). Resolution and stereoselective binding of enantiomers: M. Salman et al., J. Med. Chem. 29, 1801 (1986). Absolute configuration: N. Srivastava et al., Bioorg. Med. Chem. Lett. 6, 1747 (1996). HPLC determn in serum and milk: J. Lal et al., J. Chromatogr. B 658, 193 (1994). Clinical pharmacokinetics: idem et al., Contraception 52, 297 (1995). Toxicity: I. M. Chak et al., Indian J. Exp. Biol. 15, 1159 (1977). Review of clinical experience: M. M. Singh, Med. Res. Rev. 21, 302-347 (2001).
Properties: Crystals from ether/petr ether, mp 99-101°, sinters ~50°.
Melting point: mp 99-101°
Derivative Type: Hydrochloride
CAS Registry Number: 51023-56-4
Manufacturers' Codes: 6720 CDRI
Molecular Formula: C30H35NO3.HCl
Molecular Weight: 494.06
Percent Composition: C 72.93%, H 7.34%, N 2.84%, O 9.72%, Cl 7.18%
Properties: White crystals, mp 165-166°. uv max (methanol): 232, 278 nm (e 3701 at 278 nm). pKa 2.1. Sol in 10 parts chloroform, 20 parts acetone, 60 parts 95% ethanol, 20 parts methanol. Practically insol in water, isobutanol, 0.1N HCl, 0.1N NaOH. LD50 i.p. in mice: 400 mg/kg (Chak).
Melting point: mp 165-166°
pKa: pKa 2.1
Absorption maximum: uv max (methanol): 232, 278 nm (e 3701 at 278 nm)
Toxicity data: LD50 i.p. in mice: 400 mg/kg (Chak)
Derivative Type: (-)-Form
CAS Registry Number: 78994-23-7
Additional Names: Levormeloxifene
Properties: Prepd as hydrochloride, mp 197°. [a] D20 -192.9° (c = 1.0 in CHCl3).
Melting point: mp 197°
Optical Rotation: [a] D20 -192.9° (c = 1.0 in CHCl3)
Therap-Cat: Oral contraceptive.
Keywords: Contraceptive (Oral).
Cephacetrile Sodium Cephaeline Cephalins Cephaloglycin Cephalonic Acid

Ormeloxifene
Ormeloxifene structure.svg
Systematic (IUPAC) name
1-[2-[4-[(3S,4R)-7-methoxy-2,2- dimethyl-3-phenyl-chroman-4-yl] phenoxy] ethyl] pyrrolidine
Clinical data
Trade names Centron, Novex-DS, Saheli, Sevista
Legal status  ?
Routes Oral
Pharmacokinetic data
Half-life 7 days
Identifiers
CAS number 78994-24-8 N
ATC code G03XC04
PubChem CID 154413
ChemSpider 32935 YesY
UNII 44AXY5VE90 YesY
KEGG D08301 YesY
ChEMBL CHEMBL301327 YesY
Synonyms Centchroman
Chemical data
Formula C30H35NO3 
Mol. mass 457.604 g/mol
 N (what is this?)  (verify)
Ormeloxifene
Background
Birth control type Anti-estrogen
First use 1991
Failure rates (first year)
Perfect use 2%
Typical use 9%
Usage
Duration effect One week
Reversibility Immediate
User reminders Taken twice weekly for first 13 weeks
Clinic review Annually
Advantages and disadvantages
STD protection No
Periods May disrupt
Weight No proven effect
Medical notes
Only approved as a contraceptive in India

Ormeloxifene (also known as centchroman) is one of the selective estrogen receptor modulators,[1] or SERMs, a class of medication which acts on the estrogen receptor. It is best known as a non-hormonal, non-steroidal oral contraceptive which is taken once per week. In India, ormeloxifene has been available as birth control since the early 1990s, and it is currently marketed there under the trade name Saheli.[2] Ormeloxifene has also been licensed under the trade names Novex-DS, Centron and Sevista.