QuickView for Norethindrone (compound)

Summary
General Info

PubChem

PubChem Compound 11865443

Name:	Norethindrone
PubChem Compound ID:	11865443
Description:	A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for contraception.
Molecular formula:	C₂₀H₂₆O₂
Molecular weight:	298.419 g/mol
Synonyms:	ZINC03831215

DrugBank

Identification

Name:	Norethindrone
Name (isomeric):	DB00717
Drug Type:	small molecule
Description:	A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for contraception.
Brand:	Utovlan, Orlest, Utovlar, Noraethisteronum, Brevinor-1 21, Menzol, Ciclovulan, Primolut N, Brevinor-1 28, Norluten, ENT, Norimin, Loestrin 24 Fe, Trinovum 21, Ortho-Novum 1 50, Ortho 7 7 7, Conludaf, Conludag, Errin, Norethynodrone, Microneth, Anovulatorio, Palonyl, Estrinor, Micronett, Necon, Anhydrohydroxynorprogesterone, Norethin, Aygestin, Norpregneninlone, Binovum, Genora, Noresthisterone, Anovule, Noretisterone [Dcit], Loestrin, Ethynylmortestosterone, Norcolut, Norethindrone Norethisterone, Normapause, Norcept-E, Noriday, Nor-Qd, Noretisterona [INN-Spanish], Noriday 28, Norethisterone [Progestins], Ortho-Novum 1 35, Proluteasi, Norethyndron, Ortho 1 35, Norgestin, Conceplan, Nodiol, Jenest-28, Ovysmen, Tri-Norinyl, Minovlar, Micronor, Norlutate, Nelova, Norethynodron, Norpregneninolone, Demulen, Norethisteronum [INN-Latin], Triella, Norethindrone Acetate, Synphase, Ovysmen 0.5 35, Nor-Q.D., Norlutin, Gencept, Ovysmen 1 35, Synphasic 28, Norethisterone, Perovex, Gestest, Brevinor, Norethisteron, Ethynylnortestosterone, Trinovum, Mini-Pe, Ortho-Novum, Brevinor 21, Norlestrin, Brevinor 28, Neocon, Modicon, Jenest, Norfor, Milli, Primolut-N, Norethin 1/35 E, N.E.E., Brevicon, Norluton, Noralutin, NET, Micronovum, Camila, Ortho-Novum 7 7 7, Norinyl, Ethinylnortestosterone, Norpregneninotone, Mini-Pill, Norethadrone, Norcept, Norethin 1/50 M, Ovcon
Brand name mixture:	Estalis 250/50 Mcg(Estradiol + Norethindrone Acetate), Norinyl 1/50 (28 day)(Mestranol + Norethindrone), Synphasic (28 day)(Ethinyl Estradiol + Norethindrone), Brevicon 0.5/35 Tablets (28 day)(Ethinyl Estradiol + Norethindrone), Minestrin 1/20 28(Ethinyl Estradiol + Norethindrone Acetate), Brevicon 0.5/35 (21 day)(Ethinyl Estradiol + Norethindro... show more » Estalis 250/50 Mcg(Estradiol + Norethindrone Acetate), Norinyl 1/50 (28 day)(Mestranol + Norethindrone), Synphasic (28 day)(Ethinyl Estradiol + Norethindrone), Brevicon 0.5/35 Tablets (28 day)(Ethinyl Estradiol + Norethindrone), Minestrin 1/20 28(Ethinyl Estradiol + Norethindrone Acetate), Brevicon 0.5/35 (21 day)(Ethinyl Estradiol + Norethindrone), Ortho 7/7/7 Tablets (28 day)(Ethinyl Estradiol + Norethindrone), Brevicon 0.5/35 (28 day)(Ethinyl Estradiol + Norethindrone), Ortho 10/11 Tablets (21 day)(Ethinyl Estradiol + Norethindrone), Loestrin 1.5/30 28-day Pack(Ethinyl Estradiol + Norethindrone Acetate), Select 1/35 (21 day)(Ethinyl Estradiol + Norethindrone), Ortho-Novum 1/50 Tablets (21 day)(Mestranol + Norethindrone), Ortho-Novum 1/50 Tablets (28 day)(Mestranol + Norethindrone), Synphasic (21 day)(Ethinyl Estradiol + Norethindrone), Select 1/35 (28 day)(Ethinyl Estradiol + Norethindrone), Loestrin 1.5/30 21-day Pack(Ethinyl Estradiol + Norethindrone Acetate), Brevicon 1/35 Tablets (28 day)(Ethinyl Estradiol + Norethindrone), Brevicon 0.5/35 Tablets (21 day)(Ethinyl Estradiol + Norethindrone), Norinyl 1/50 (21 day)(Mestranol + Norethindrone), Brevicon 1/35 Tablets (21 day)(Ethinyl Estradiol + Norethindrone), Femhrt 1/5(Ethinyl Estradiol + Norethindrone Acetate), Estalis Sequi(Estradiol + Norethindrone Acetate), Minestrin 1/20 21(Ethinyl Estradiol + Norethindrone Acetate), Norinyl 1/50 - 28-day pack(Mestranol + Norethindrone), Estracomb(Estradiol + Norethindrone Acetate), Norinyl 1/50 - 21-day pack(Mestranol + Norethindrone), Estalis 140/50 Mcg(Estradiol + Norethindrone Acetate), Ortho 10/11 Tablets (28 day)(Ethinyl Estradiol + Norethindrone), Ortho 0.5/35 Tablets (21 day)(Ethinyl Estradiol + Norethindrone), Ortho 7/7/7 Tablets (21 day)(Ethinyl Estradiol + Norethindrone), Ortho 1/35 Tablets (21 day)(Ethinyl Estradiol + Norethindrone), Ortho 0.5/35 Tablets (28 day)(Ethinyl Estradiol + Norethindrone), Ortho 1/35 Tablets (28 day)(Ethinyl Estradiol + Norethindrone) show less «
Category:	Progestins, Contraceptives, Oral, Synthetic
CAS number:	68-22-4

Pharmacology

Indication:	For use as an oral contraceptive in the prevention of pregnancy.
Pharmacology:	Norethindrone is a synthetic oral progestin. It is used for contraception or to treat such conditions as secondary amenorrhea, abnormal uterine bleeding, and endometriosis. As an oral contraceptive, norethindrone is available as either a single agent or in combination with an estrogen.
Mechanism of Action:	Progestins diffuse freely into target cells and bind to the progesterone receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory... show more » Progestins diffuse freely into target cells and bind to the progesterone receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH surge. show less «
Absorption:	Absolute oral bioavailability approximately 64%
Protein binding:	>95%
Biotransformation:	Hepatic
Half Life:	7 hours
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Carbamazepine	This product may cause a slight decrease of contraceptive effect
Tretinoin	Oral Tretinoin may decrease the effect of oral contraceptive, Norethindrone. An alternate form of contraception should be used during concomitant therapy.
Talbutal	This product may cause a slight decrease of contraceptive effect
St. John's Wort	St. John's Wort could reduce the contraceptive effect
Rifabutin	Rifabutin may decrease the contraceptive effect of norethindrone. Hormonal contraception should not be solely relied on alone during concomitant therapy with rifabutin.

Carbamazepine	This product may cause a slight decrease of contraceptive effect
Tretinoin	Oral Tretinoin may decrease the effect of oral contraceptive, Norethindrone. An alternate form of contraception should be used during concomitant therapy.
Talbutal	This product may cause a slight decrease of contraceptive effect
St. John's Wort	St. John's Wort could reduce the contraceptive effect
Rifabutin	Rifabutin may decrease the contraceptive effect of norethindrone. Hormonal contraception should not be solely relied on alone during concomitant therapy with rifabutin.
Butabarbital	This product may cause a slight decrease of contraceptive effect
Rifampin	This product may cause a slight decrease of contraceptive effect
Colesevelam	Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Progestins). Administer oral progestin-containing contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness.
Aprobarbital	This product may cause a slight decrease of contraceptive effect
Hexobarbital	This product may cause a slight decrease of contraceptive effect
Amobarbital	This product may cause a slight decrease of contraceptive effect
Troglitazone	Possible loss of contraceptive effect
Thiopental	Thiopental may decrease the effect of Norethindrone. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Warfarin	Norethindrone may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if norethindrone is initiated, discontinued or dose changed.
Griseofulvin	This product may cause a slight decrease of contraceptive effect
Phenytoin	This product may cause a slight decrease of contraceptive effect
Methohexital	This product may cause a slight decrease of contraceptive effect
Phenobarbital	This product may cause a slight decrease of contraceptive effect
Bexarotene	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norethindrone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Butethal	This product may cause a slight decrease of contraceptive effect
Fosphenytoin	This product may cause a slight decrease of contraceptive effect
Lamotrigine	The oral contraceptive decreases the effect of lamotrigine
Bosentan	Bosentan may decrease the contraceptive effect of norethindrone. Hormonal contraception should not be relied on alone during concomitant therapy with bosentan.
Acitretin	Acitretine may cause a loss of contraceptive effect
Artemether	Artemether may decrease the effectiveness of norethindrone by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Methylphenobarbital	This product may cause a slight decrease of contraceptive effect
Heptabarbital	This product may cause a slight decrease of contraceptive effect
Rifapentine	This product may cause a slight decrease of contraceptive effect
Tizanidine	The contraceptive increases the effect of tizanidine
Pentobarbital	This product may cause a slight decrease of contraceptive effect
Primidone	This product may cause a slight decrease of contraceptive effect
Ethotoin	This product may cause a slight decrease of contraceptive effect
Butalbital	This product may cause a slight decrease of contraceptive effect
Pioglitazone	Possible loss of contraceptive effect
Secobarbital	This product may cause a slight decrease of contraceptive effect
Mephenytoin	This product may cause a slight decrease of contraceptive effect

show less «

Targets

Progesterone receptor

Enzymes

Transporters

Multidrug resistance protein 1