Contraception (Birth Control) and Family Planning PubHealthInfo

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PubHealth.info® (a subsidiary of PakMed) presents scientific information mainly based on abstracts of articles published on a variety of public health issues/topics, particularly encompassing population planning, disease prevention, maternal and child health, and communicable and non-communicable diseases (like HIV AIDS, malaria, etc) that are affecting a significant portion of population in developing and developed countries. Here you can find abstracts of articles published on a variety of public health topics under category "Contraception (Birth Control) and Family Planning". Contraception (birth control) is a regimen of one or more actions, devices, or medications followed in order to deliberately prevent or reduce the likelihood of a woman becoming pregnant or giving birth. Therefore contraception is the utilization of various and sundry surgical procedures, devices, practices, agents, or drugs with the intention of preventing conception or impregnation (pregnancy). Methods and intentions typically termed birth control may be considered a pivotal ingredient to family planning. Birth control is a controversial political and ethical issue in many cultures and religions, and although it is generally less controversial than abortion specifically.

YEAR: 1994

CATEGORY: Contraception (Birth Control) and Family Planning

TITLE

An X-ray crystallographic study of the nonsteroidal contraceptive agent

centchroman.

AUTHORS

Ray S; Tandon A; Dwivedy I; Wilson SR; O'Neil JP; Katzenellenbogen JA

SOURCE

JOURNAL OF MEDICINAL CHEMISTRY. 1994 Mar 4;37(5):696-700.

ABSTRACT

The authors have determined an x-ray crystal structure for the N-methyl iodide derivative of the nonsteroidal

contraceptive centchroman. The pendant aromatic substituents on C-3 and C-4 of the chroman system are nearly

perpendicular to the plane of the chroman system, an orientation expected in such a chroman, but perturbed to some

degree by the gem dimethyl substituents at C-2. Structural superposition with other nonsteroidal antiestrogens,

tamoxifen and nafoxidine, shows a similar disposition of the tertiary amine side chains responsible for antagonist

activity. The aryl rings also show good superposition, but in contrast to tamoxifen and nafoxidine, which have the

potential for ring double bond conjugation, the centchroman aryl rings show a larger dihedral twist. While different

superpositions between the enantiomers of centchroman and the bioactive enantiomer of estradiol (d-estradiol,

8beta,9alpha,13beta,14alpha,17beta) are possible, when the chroman ring system is positioned over the AB rings of

estradiol, then (3R-4R)-centchroman makes the best fit. The aryl substituents in both enantiomers make comparable

overlays with the steroidal skeleton, but the axial methyl group at C-2 in (3R-4R)-centchroman is directed downward

along the C-7alpha axis of estradiol, a site where many substituents are known to be well tolerated by the estrogen

receptor, while in the 3S-4S-enantiomer, this methyl group is projected upward. Thus, the authors suggest that the

bioactive l-enantiomer of centchroman will have the 3R-4R absolute configuration. (PubHealth.info Document ID:

CONT2T 4517-06)

PubHealth.info NOTE: The author(s) of this article titled, "An X-ray crystallographic study of the nonsteroidal

contraceptive agent centchroman.", is(are) Ray S; Tandon A; Dwivedy I; Wilson SR; O'Neil JP; Katzenellenbogen

JA. The source of this article is "JOURNAL OF MEDICINAL CHEMISTRY. 1994 Mar 4;37(5):696-700.". This article

was published in 1994 in English language(s). (PubHealth.info® Document ID: CONT2T 4517-06. All rights reserved

with PubHealth.info) PIN: 9517

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