Chlormadinone

Structural formula
General
Non-proprietary name	Chlormadinone
other names	6-chloro-17 α- hydroxy-17 β -pregna-4,6-diene-3,20-dione
Molecular formula	C 21 H 27 ClO 3
External identifiers / databases
EC number	217-802-3
ECHA InfoCard	100.016.185
PubChem	5284533
ChemSpider	4447590
Wikidata	Q905012
Drug information
ATC code	G03 DB06 G03 AA16 ; G03 AB07 G03 FA20 ; G03 FB03 ;
Drug class	Progestins
properties
Molar mass	362.89 g mol −1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 351-360
	P: 201-281-308 + 313
Toxicological data	> 10000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlormadinone is a synthetically produced sex hormone ( progestin ). It is used to treat hormonal disorders in women, for hormone replacement therapy during menopause and in combination with ethinylestradiol for hormonal contraception ( birth control pills ).

Mode of action

Chlormadinone has an anti- estrogenic effect. It reduces the mobility of the fallopian tubes and makes the cervical mucus thicker. The egg transport is disrupted and the sperm cells from entering the uterus are prevented. In higher doses, chlormadinone inhibits the release of gonadotropic hormones from the pituitary gland . The gonadotropic hormones LH and FSH control the activity of the ovaries (e.g. ovulation) and transformation processes in the uterine lining .

Chlormadinone also has a partial antiandrogenic effect, which is based on the substance's ability to displace androgens from their receptors. This is important for the therapy of androgen-dependent diseases such as hirsutism , androgenetic hair loss and acne seborrhoica .

A pregnancy-sustaining effect, as with other synthetic gestagens, could not be proven for chlormadinone.

application areas

Chlormadinone is used as chlormadinone acetate in drugs. It is indicated in hormone replacement therapy for menopausal symptoms, for the treatment of growths of the uterine lining , irregular cycles and menstrual cramps (e.g. oligomenorrhea , polymenorrhea , hypermenorrhea , dysmenorrhea , secondary amenorrhea ) and painful feelings of tightness in the chest ( mastodynia ) . In combination with ethinylestradiol , it is used for hormonal contraception.

Patients suffering from androgenetic diseases (such as acne, see section on mode of action ) can benefit therapeutically from the anti-androgenic effect of chlormadinone acetate.

Trade names

Combination preparations

Balanca (D, A), Belara (D, A, CH), Bellissima (D), Chantal (D), Chariva (D), Esticia (D), Enriqa (lactose-free) (D), Eufem (D), Lilia (D), Madinette (D), Minette (D) Mona Hexal (D), Neo Eunomin (D), Pink Luna (D)

Monopreparations

Chlormadinone 2mg fem (D)

Web links

Combined contraception with new progestin: Belara ( Memento from January 15, 2009 in the Internet Archive )

Individual evidence

↑ ^a ^b data sheet Chlormadinone acetate at Sigma-Aldrich , accessed on August 17, 2019 ( PDF ).
↑ Entry on chlormadinone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ JC Frölich, W. Kirch (ed.): Practical medicine therapy , Springer-Verlag, 2003, ISBN 3-540-01025-4 , p. 435.
↑ Treatment of acne vulgaris . ( Memento of November 27, 2015 in the Internet Archive ) In: arznei-telegram No. 1 (1997).
^ Druckmann R: Profile of the progesterone derivative chlormadinone acetate - pharmocodynamic properties and therapeutic applications. . In: Contraception . 79, 2009, pp. 272-281. PMID 19272496 .

[Sigma-1] ta sheet Chlormadinone acetate at Sigma-Aldrich , accessed on August 17, 2019 ( PDF ).

[ChemIDplus-2] Entry on chlormadinone in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[3] JC Frölich, W. Kirch (ed.): Practical medicine therapy , Springer-Verlag, 2003, ISBN 3-540-01025-4 , p. 435.

[4] Treatment of acne vulgaris . ( Memento of November 27, 2015 in the Internet Archive ) In: arznei-telegram No. 1 (1997).

[5] Druckmann R: Profile of the progesterone derivative chlormadinone acetate - pharmocodynamic properties and therapeutic applications. . In: Contraception . 79, 2009, pp. 272-281. PMID 19272496 .