Norethisterone

Identification

Summary

Norethisterone is a synthetic second-generation progestin used for contraception, prevention of endometrial hyperplasia in hormone replacement therapy, and in the treatment of other hormone-mediated illnesses such as endometriosis.

Brand Names
Activella 1/0.5 28 Day, Activelle, Alyacen 1/35, Alyacen 7/7/7, Amabelz 0.5/0.1 28 Day, Aranelle 28, Aurovela, Aurovela Fe, Aygestin, Balziva 28 Day, Blisovi 21 Fe 1.5/30 28 Day Pack, Blisovi 21 Fe 1/20 28 Day Pack, Blisovi 24 Fe 1/20 28 Day, Brevicon, Briellyn 28 Day, Camila 28 Day, Charlotte 24 Fe Chewable 28 Day, Combipatch, Cyclafem 1/35 28 Day, Cyclafem 7/7/7 28 Day, Cyonanz 28 Day, Dasetta 1/35 28 Day, Dasetta 7/7/7 28 Day, Deblitane 28 Day, Emzahh 28 Day, Errin 28 Day, Estalis, Etyqa 0.5/0.1 28 Day, Femcon Fe 28 Day, Femhrt 0.5/2.5 28 Day, Finzala 24 Fe Chewable 28 Day, Fyavolv, Gemmily 28 Day, Hailey 1.5/30 21 Day, Hailey 24 Fe 28 Day, Hailey Fe 1.5/30 28 Day, Hailey Fe 1/20 28 Day, Heather 28 Day, Incassia, Jencycla 28 Day, Jinteli, Junel 1.5/30 21 Day, Junel 1/20 21 Day, Junel Fe 1.5/30 28 Day, Junel Fe 1/20 28 Day, Junel Fe 24 1/20 28 Day, Kaitlib Fe 28 Day, Larin 1.5/30, Larin 1/20, Larin 24 Fe 1/20, Larin Fe 1.5/30, Larin Fe 1/20, Layolis Fe 28, Leena 28 Day, Lo Loestrin Fe 28 Day, Loestrin 1.5/30 21 Day, Loestrin 24 Fe 28 Day, Loestrin Fe 1/20 28 Day, Lolo, Lomedia 24 Fe, Lopreeza 1/0.5 28 Day, Lupaneta Pack 1-month, Lyleq 28 Day, Lyza, Melodetta 24 Fe Chewable 28 Day, Merzee 28 Day, Mibelas 24 Fe Chewable 28 Day, Microgestin 1.5/30 21 Day, Microgestin 1/20 21 Day, Microgestin 24 Fe 28 Day, Microgestin Fe 1.5/30 28 Day, Microgestin Fe 1/20 28 Day, Mimvey, Minastrin 24 Fe Chewable 28 Day, Myfembree, Necon 0.5/35 28 Day, Necon 1/35 28 Day, Necon 7/7/7 28 Day, Nexesta Fe 28 Day, Nora-BE 28 Day, Norlutate, Norlyda 28 Day, Norlyroc 28 Day, Nortrel 1/35 21 Day, Nortrel 1/35 28 Day, Nortrel 7/7/7 28 Day, Nylia 1/35 28 Day, Nylia 7/7/7 28 Day, Oriahnn 28 Day Kit, Ortho Micronor, Ortho Micronor 28 Day, Ortho-novum 7/7/7 28 Day, Philith 28 Day, Pirmella 1/35 28 Day, Pirmella 7/7/7 28 Day, Rhuzdah 28 Day, Select, Sharobel 28 Day, Synphasic, Tarina 24 Fe 1/20 28 Day, Tarina Fe 1/20 28 Day, Taysofy 28 Day, Taytulla 28 Day, Tilia Fe, Tri-legest 28 Day, Tulana 28 Day, Vyfemla 28 Day, Wera 28 Day, Wymzya Fe 28 Day, Zenchent
Generic Name
Norethisterone
DrugBank Accession Number
DB00717
Background

Norethisterone, also known as norethindrone, is a synthetic progestational hormone belonging to the 19-nortestosterone-derived class of progestins.8 It is further classified as a second-generation progestin, along with levonorgestrel and its derivatives, and is the active form of several other progestins including norethynodrel and lynestrenol.8 Norethisterone mimics the actions of endogenous progesterone, albeit with a greater potency,5 and is used on its own or in combination with estrogen derivatives in a variety of applications including contraception and hormone replacement therapy.14,15,16,19 First derived in 1951 in Mexico City, norethisterone was originally intended for use as a remedy for irregular menstruation and endometriosis, and was not marketed for use as an oral contraceptive until 1962.21

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 298.4192
Monoisotopic: 298.193280076
Chemical Formula
C20H26O2
Synonyms
  • (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one
  • 17-hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one
  • 17-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one
  • 17-α-ethynyl-17-hydroxy-4-estren-3-one
  • 17-α-ethynyl-19-norandrost-4-en-17-β-ol-3-one
  • 17-α-ethynyl-19-nortestosterone
  • 17-α-ethynyl-4-estren-17-ol-3-one
  • 17-β-hydroxy-19-norpregn-4-en-20-yn-3-one
  • 17α-ethinyl-19-nortestosterone
  • 17α-ethinylestra-4-en-17β-ol-3-one
  • 17α-ethynyl-17-hydroxy-4-estren-3-one
  • 17α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-one
  • 17α-ethynyl-19-nor-4-androsten-17β-ol-3-one
  • 17α-ethynyl-19-norandrost-4-en-17β-ol-3-one
  • 17α-ethynyl-19-nortestosterone
  • 17α-ethynyl-4-estren-17-ol-3-one
  • 17β-hydroxy-19-norpregn-4-en-20-yn-3-one
  • 19-nor-17-α-ethynyl-17-β-hydroxy-4-androsten-3-one
  • 19-nor-17-α-ethynylandrosten-17-β-ol-3-one
  • 19-nor-17-α-ethynyltestosterone
  • 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one
  • 19-nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one
  • 19-nor-17α-ethynylandrosten-17β-ol-3-one
  • 19-nor-17α-ethynyltestosterone
  • 19-nor-ethindrone
  • 19-norethisterone
  • 4-estren-17α-ethynyl-17β-ol-3-one
  • Norethindrone
  • Norethisteron
  • Noréthistérone
  • Norethisterone
  • Norethisteronum
  • Noretisterona
External IDs
  • NSC-9564
  • SC-4640

Pharmacology

Indication

Norethisterone is indicated as an oral contraceptive when given as monotherapy14 or in combination with an estrogen component, such as ethinylestradiol or estradiol.18,19 In combination with an estrogen component, oral norethisterone is also indicated as a hormone replacement therapy in the treatment of postmenopausal osteoporosis and moderate-to-severe vasomotor symptoms arising from menopause.16 When applied via transdermal patch, the combination of norethisterone and estradiol is indicated for the treatment of hypoestrogenism, vulvovaginal atrophy, and moderate-severe vasomotor symptoms.15

Norethisterone, taken in combination with intramuscular leuprolide, is also indicated for the symptomatic treatment of endometriosis-related pain.17

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for symptomatic treatment ofEndometriosis related painCombination Product in combination with: Ethanol (DB00898), Leuprolide (DB00007)•••••••••••••••••••••• ••••••••••• •••••••• •••••••• ••••••
Used in combination to manageHeavy menstrual bleedingCombination Product in combination with: Estradiol (DB00783), Relugolix (DB11853)•••••••••••••••••••••••••••••••
Used in combination to treatModerate to severe vasomotor symptomsCombination Product in combination with: Estradiol (DB00783)•••••••••••••••••
Used in combination to preventOsteoporosisCombination Product in combination with: Estradiol valerate (DB13956)•••••••••••••••••• •••••••••••••••••••••••• •• •• •••••••••• •• ••••• •••••••••• •••• •••• •• ••••••••••••••
Used in combination to preventPostmenopausal osteoporosis (pmo)Combination Product in combination with: Ethinylestradiol (DB00977)••••••••••••••••••
Associated Therapies
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Pharmacodynamics

Norethisterone is a synthetic oral progestin used for contraception or to treat other hormone-related conditions such as menopausal symptoms and endometriosis. As a synthetic progestin, norethisterone acts similarly to endogenous progesterone but with a much higher potency - it acts at the pelvic level to alter cervical and endometrial function, as well as via the inhibition of pituitary hormones that play a role in follicular maturation and ovulation.14 A small increase in the risk of developing breast cancer has been observed in patients using combined oral contraceptives, with some evidence also implicating progestin-only pills - patients starting hormonal contraception should be advised of this risk and should employ routine breast self-examinations to check for evidence of any developing masses.14

Mechanism of action

On a molecular level, progestins like norethisterone exert their effects on target cells via binding to progesterone receptors that result in downstream changes to target genes.16 Target cells are found in the reproductive tract, breast, pituitary, hypothalamus, skeletal tissue, and central nervous system.16 Contraceptive efficacy is derived mainly from changes to the cervical mucus, wherein norethisterone increases the cell content and viscosity of the mucous to impede sperm transport and migration.14 Norethisterone also induces a variety of changes to the endometrium - including atrophy, irregular secretion, and suppressed proliferation - that make it inhospitable for implantation.14,12 Working via a negative feedback loop, norethisterone also acts on both the hypothalamus and anterior pituitary to suppress the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. Suppression of these hormones prevents follicular development, ovulation, and corpus luteum development.12

When used as a component of hormone replacement therapy in menopausal women, norethisterone’s value is mainly in suppressing the growth of the endometrium.13 As estrogen stimulates endometrial growth, the unopposed use of estrogen in postmenopausal women with an intact uterus can lead to endometrial hyperplasia which can increase the risk of endometrial cancer. The addition of a progestin to a hormone replacement therapy in this population protects against this endometrial hyperplasia and, therefore, lowers the risk associated with the use of hormone replacement therapies.

Norethisterone, along with other progestins and endogenous progesterone, has a low affinity for other steroid receptors, such as the androgen receptor and glucocorticoid receptor.8,5 While affinity and agonistic activity at these receptors is minimal, it is thought that androgen receptor agonism is responsible for some of the adverse effects observed with progestin use (e.g. acne, serum lipid changes).8

TargetActionsOrganism
AProgesterone receptor
agonist
Humans
UAndrogen receptor
agonist
Humans
UGlucocorticoid receptor
agonist
Humans
Absorption

The Cmax of norethisterone following oral administration of a single dose ranges from 5.39 to 7.36 ng/mL with a Tmax of 1-2 hours.14,16,19 AUC0-24 values following single oral doses range from approximately 30 to 37 ng*hr/mL.14,16,19 The oral bioavailability of norethisterone is approximately 64%.19 When applied transdermally, norethisterone is well-absorbed through the skin, reaches steady-state concentrations within 24 hours, and has a Cmax ranging from 617 to 1060 pg/mL at steady state.15

Norethisterone is often formulated as norethisterone acetate, which is completely and rapidly deacetylated to norethisterone following oral administration - the disposition of norethisterone acetate is indistinguishable from that of orally administered norethisterone.19

Volume of distribution

The volume of distribution of norethisterone is approximately 4 L/kg.4,19 Sulfated metabolites of norethisterone, as well as small quantities of parent drug, have been shown to distribute into breast milk.11

Protein binding

Norethisterone is 38% bound to sex hormone-binding globulin and 61% bound to albumin.4,19

Metabolism

Norethisterone is extensively metabolized, primarily in the liver, to a number of metabolites via partial and total reduction of its A-ring.6 The enzymes predominantly involved are 3α- and 3β-hydroxysteroid dehydrogenase (HSD) as well as 5α- and 5β-reductase.6,5 The 5α-reduced metabolites, including 5α-dihydronorethisterone and its derivatives, appear to carry biological activity while the 5β-reduced metabolites appear inactive.5 Norethisterone and its metabolites are also extensively conjugated - most of the plasmatic metabolites are sulfate conjugates, while most of the urinary metabolites are glucuronide conjugates.4,19 The major metabolites in plasma are a disulfate conjugate of 3α,5α-tetrahydronorethisterone and a monosulfate conjugate of 3α,5β-tetrahydronorethisterone, while the major metabolite(s) in the urine are comprised of glucuronide and/or sulfate conjugates of 3α,5β-tetrahydronorethisterone.10

Norethisterone has also been observed to undergo some degree of metabolism via the cytochrome P450 enzyme system, predominantly by CYP3A4 and, to a much lesser extent, by CYP2C19, CYP1A2, and CYP2A6.7 The metabolites generated by these reactions have not been fully characterized.

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Route of elimination

Following administration of radio-labeled norethisterone, slightly more than 50% of the administered dose was eliminated in the urine and 20-40% was eliminated in the feces.1

Half-life

The half-life of norethisterone has been variably estimated as 8-10 hours.4,3,8,14,18

Clearance

The plasma clearance of norethisterone has been estimated as 0.4 L/hr/kg,4,19 and the intrinsic clearance is approximately 73-81 L/h.9

Adverse Effects
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Toxicity

The oral LD50 in mice 6 g/kg and the TDLo in human women is 42 mg/kg.20 There have been no reports of serious ill effects following overdose of oral contraceptives, including following ingestion by children.19,18 Symptoms of overdosage are likely to be consistent with the adverse effect profile of the contraceptive and may, therefore, include significant nausea and/or vomiting.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Norethisterone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Norethisterone can be increased when combined with Abatacept.
AbciximabThe risk or severity of adverse effects can be increased when Norethisterone is combined with Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Norethisterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Norethisterone.
Food Interactions
  • Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Norethisterone acetate9S44LIC7OJ51-98-9IMONTRJLAWHYGT-ZCPXKWAGSA-N
Product Images
International/Other Brands
Conludag / Micronovum / Mini-PE / Mini-pill / Norcolut / Noriday / Norluten / Norlutin / Primolut-N / Utovlan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
JencyclaTablet0.35 mgOralLupin Pharma2015-09-14Not applicableCanada flag
JolivetteTablet0.35 mg/1OralActavis Pharma, Inc.2003-03-012020-12-31US flag
MaeveTablet0.35 mgOralGlenmark Pharmaceuticals, Inc2022-12-16Not applicableCanada flag
MicronorTablet0.35 mg/1OralPhysicians Total Care, Inc.2003-09-17Not applicableUS flag
Micronor Tablets 28-dayTablet0.35 mgOralJanssen Pharmaceuticals1972-12-312020-07-09Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AffodelTablet0.35 mg/1OralNaari Pte. Limited2022-12-31Not applicableUS flag
AygestinTablet5 mg/1OralTeva Women's Health LLC2003-06-122024-08-31US flag
CamilaTablet0.35 mg/1OralMayne Pharma Inc.2016-08-032020-04-30US flag
CamilaTablet0.35 mg/1OralTeva2002-10-302018-02-28US flag
CamilaTablet0.35 mg/1OralPhysicians Total Care, Inc.2003-06-19Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ActivellaNorethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1)Tablet, film coatedOralNovo Nordisk2007-04-092017-04-30US flag
ActivellaNorethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1)Tablet, film coatedOralAmneal Pharmaceuticals LLC2019-05-01Not applicableUS flag
ActivellaNorethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1)Tablet, film coatedOralGemini Laboratories, LLC2016-05-122019-08-31US flag
ActivellaNorethisterone acetate (0.5 mg/1) + Estradiol (1 mg/1)Tablet, film coatedOralNovo Nordisk2003-07-222018-10-31US flag
ActivellaNorethisterone acetate (0.5 mg/1) + Estradiol (1 mg/1)Tablet, film coatedOralAmneal Pharmaceuticals LLC2019-05-01Not applicableUS flag

Categories

ATC Codes
H01CC53 — Elagolix, estradiol and norethisteroneH01CC54 — Relugolix, estradiol and norethisteroneG03AA05 — Norethisterone and ethinylestradiolG03DC02 — NorethisteroneG03AB04 — Norethisterone and ethinylestradiolG03AC01 — NorethisteroneG03FA01 — Norethisterone and estrogenG03FB05 — Norethisterone and estrogen
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, tertiary alcohol, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:7627) / Pregnane and derivatives [Fig], C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05028) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030097)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
T18F433X4S
CAS number
68-22-4
InChI Key
VIKNJXKGJWUCNN-XGXHKTLJSA-N
InChI
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
IUPAC Name
(1R,3aS,3bR,9aR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

References

Synthesis Reference

Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F: Steroids LIV. Synthesis of 19-nor-17α-ethynyltestosterone and 19-nor-17α-methyltestosterone. Am J Obstet Gynecol. 2006. 194(1):289.

General References
  1. Stanczyk FZ, Roy S: Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids. Contraception. 1990 Jul;42(1):67-96. [Article]
  2. Frohlich M, Albermann N, Sauer A, Walter-Sack I, Haefeli WE, Weiss J: In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem Pharmacol. 2004 Dec 15;68(12):2409-16. doi: 10.1016/j.bcp.2004.08.026. [Article]
  3. Stanczyk FZ, Mroszczak EJ, Ling T, Runkel R, Henzl M, Miyakawa I, Goebelsmann U: Plasma levels and pharmacokinetics of norethindrone and ethinylestradiol administered in solution and as tablets to women. Contraception. 1983 Sep;28(3):241-51. doi: 10.1016/0010-7824(83)90065-3. [Article]
  4. Barra F, Scala C, Ferrero S: Current understanding on pharmacokinetics, clinical efficacy and safety of progestins for treating pain associated to endometriosis. Expert Opin Drug Metab Toxicol. 2018 Apr;14(4):399-415. doi: 10.1080/17425255.2018.1461840. Epub 2018 Apr 10. [Article]
  5. Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
  6. Walker CJ, Cowan DA, James VH, Lau JC, Kicman AT: Doping in sport: 3. Metabolic conversion of oral norethisterone to urinary 19-norandrosterone. Steroids. 2009 Mar;74(3):341-9. doi: 10.1016/j.steroids.2008.11.008. Epub 2008 Nov 19. [Article]
  7. Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
  8. Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
  9. Kuhnz W, Gieschen H: Predicting the oral bioavailability of 19-nortestosterone progestins in vivo from their metabolic stability in human liver microsomal preparations in vitro. Drug Metab Dispos. 1998 Nov;26(11):1120-7. [Article]
  10. Sahlberg BL, Landgren BM, Axelson M: Metabolic profiles of endogenous and ethynyl steroids in plasma and urine from women during administration of oral contraceptives. J Steroid Biochem. 1987 May;26(5):609-17. doi: 10.1016/0022-4731(87)90014-8. [Article]
  11. Sahlberg BL: The characterization of sulphated metabolites of norethindrone in human milk after oral administration of contraceptive steroids. J Steroid Biochem. 1987 Apr;26(4):481-5. doi: 10.1016/0022-4731(87)90060-4. [Article]
  12. Rivera R, Yacobson I, Grimes D: The mechanism of action of hormonal contraceptives and intrauterine contraceptive devices. Am J Obstet Gynecol. 1999 Nov;181(5 Pt 1):1263-9. [Article]
  13. Gompel A: Progesterone, progestins and the endometrium in perimenopause and in menopausal hormone therapy. Climacteric. 2018 Aug;21(4):321-325. doi: 10.1080/13697137.2018.1446932. Epub 2018 Mar 27. [Article]
  14. DPD Approved Drugs: Jencycla oral tablets [Link]
  15. FDA Approved Drug Products: CombiPatch® transdermal system [Link]
  16. FDA Approved Drug Products: Femhrt® tablets [Link]
  17. FDA Approved Drug Products: Lupaneta Pack for intramuscular and oral use [Link]
  18. FDA Approved Drug Products: Generess Fe chewable tablets [Link]
  19. FDA Approved Drug Products: Lo Loestrin Fe oral tablets [Link]
  20. CaymanChem: Norethisterone MSDS [Link]
  21. The Embryo Project Encyclopedia: Progestin [Link]
Human Metabolome Database
HMDB0014855
KEGG Drug
D00182
KEGG Compound
C05028
PubChem Compound
6230
PubChem Substance
46504816
ChemSpider
5994
BindingDB
50148732
RxNav
7514
ChEBI
7627
ChEMBL
CHEMBL1162
ZINC
ZINC000085205451
Therapeutic Targets Database
DAP001212
PharmGKB
PA450651
PDBe Ligand
NDR
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Norethisterone
PDB Entries
1sqn / 2w8y

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceContraception / Fertility1
4CompletedOtherContraception1
4CompletedPreventionBacterial Vaginosis (BV) / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionBreastfeeding / Contraception1
4CompletedPreventionChanges in menstrual flow1

Pharmacoeconomics

Manufacturers
  • Parke davis div warner lambert co
  • Barr laboratories inc
  • Glenmark generics ltd
  • Ortho mcneil janssen pharmaceuticals inc
  • Watson laboratories inc
  • Duramed research inc
  • Glenmark generics ltd india
  • Warner Chilcott
Packagers
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Breckenridge Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Duramed
  • Glenmark Generics Ltd.
  • Innovative Manufacturing and Distribution Services Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Novartis AG
  • Noven Pharmaceuticals Inc.
  • Novo Nordisk Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • Patheon Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmaceutics International Inc.
  • Pharmacia Inc.
  • Physician Partners Ltd.
  • Physicians Total Care Inc.
  • Qualitest
  • Quality Care
  • Redpharm Drug
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Warner Chilcott Co. Inc.
  • Watson Pharmaceuticals
  • WC Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet, coatedOral
Kit; tabletOral
TabletOral0.35 mg/1
Patch, extended releaseTransdermal
Kit; tablet, film coatedOral
PlasterTransdermal
PatchTransdermal
Tablet, film coatedOral
TabletOral
Tablet, chewableOral
Kit; tablet, chewableOral
Kit; tablet; tablet, chewableOral
KitOral
Injection, powder, lyophilized, for suspension; kit; tabletIntramuscular; Oral; Topical
TabletOral
TabletOral0.35 mg
TabletOral5 mg/1
TabletOral350 mcg
KitOral0.35 mg/1
Kit; tablet, film coatedOral0.35 mg/1
Tablet, film coatedOral0.35 mg/1
Capsule; kitOral
TabletOral10 MG
Kit; tabletOral0.35 mg/1
Capsule, liquid filled; kitOral
TabletOral5 mg
Tablet
Tablet, film coated
Oil200 mg/1ml
Tablet, sugar coatedOral
Prices
Unit descriptionCostUnit
Ovcon-35 (28) 28 0.4-35 mg-mcg tablet Disp Pack89.09USD disp
Ovcon-50 28 50-1 mcg-mg tablet Disp Pack89.09USD disp
Loestrin 1.5/30 (21) 21 1.5-30 mg-mcg tablet Disp Pack79.32USD disp
Loestrin 1/20 (21) 21 1-20 mg-mcg tablet Disp Pack79.32USD disp
Loestrin Fe 1/20 28 1-20 mg-mcg tablet Disp Pack79.32USD disp
Loestrin Fe 1.5/30 28 1.5-30 mg-mcg tablet Disp Pack77.1USD disp
Loestrin 24 Fe 28 1-20 mg-mcg tablet Disp Pack75.15USD disp
Nor-QD 28 0.35 mg tablet Disp Pack65.87USD disp
Tri-Norinyl (28) 28 0.5/1/0.5-35 mg-mcg tablet Disp Pack62.63USD disp
Ortho-Novum 10/11 (28) 28 35 mcg tablet Disp Pack60.25USD disp
Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack59.99USD disp
Norinyl 1+35 (28) 28 1-35 mg-mcg tablet Disp Pack55.99USD disp
Ortho-Novum 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack55.99USD disp
Brevicon (28) 28 0.5-35 mg-mcg tablet Disp Pack53.0USD disp
Norinyl 1+50 (28) 28 1-50 mg-mcg tablet 1 Disp Pack = 28 Pills52.99USD disp
Necon 10/11 (28) 28 35 mcg tablet Disp Pack35.99USD disp
Ortho-Novum 7/7/7 (28) 28 0.5/0.75/1-35 mg-mcg tablet Disp Pack33.99USD disp
Necon 0.5/35 (28) 28 0.5-35 mg-mcg tablet Disp Pack32.99USD disp
Necon 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack31.99USD disp
Loestrin fe 1-20 tablet5.23USD tablet
Loestrin 21 1.5-30 tablet3.66USD tablet
Loestrin 21 1-20 tablet3.66USD tablet
Aygestin 5 mg tablet3.27USD tablet
Ovcon-35 28 tablet3.06USD tablet
Loestrin fe 1.5-30 tablet2.75USD tablet
Norethindrone Acetate 5 mg tablet2.75USD tablet
Norethindrone 5 mg tablet2.65USD tablet
Ovcon-50 28 tablet2.62USD tablet
Micronor tablet2.44USD tablet
Nor-q-d tablet2.24USD tablet
Necon 1-35-28 tablet2.11USD tablet
Modicon 28 tablet2.07USD tablet
Tri-norinyl 28 tablet2.01USD tablet
Ortho-novum 1-35-28 tablet1.9USD tablet
Brevicon 28 tablet1.8USD tablet
Norinyl 1+35-28 tablet1.73USD tablet
Norinyl 1+50-28 tablet1.73USD tablet
Demulen 1-50-21 tablet1.67USD tablet
Ortho-novum 7-7-7-21 tablet1.4USD tablet
Errin 0.35 mg tablet1.34USD tablet
Ortho-novum 7/7/7-28 tablet1.33USD tablet
Camila tablet1.32USD tablet
Jolivette tablet1.32USD tablet
Nora-be tablet1.32USD tablet
Norethindrone 0.35 mg tablet1.32USD tablet
Demulen 1-50-28 tablet1.29USD tablet
Ortho micronor tablet1.23USD tablet
Necon 0.5-35-28 tablet1.15USD tablet
Necon 7-7-7-28 tablet1.15USD tablet
Necon 1-50-28 tablet1.05USD tablet
Ortho-novum 7-7-7-28 tablet1.02USD tablet
Micronor (28 Day) 0.35 mg Tablet0.66USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6036976No2000-03-142016-12-13US flag
US6667050No2003-12-232019-04-06US flag
US7704984No2010-04-272029-02-02US flag
US6652880No2003-11-252020-03-29US flag
US7419983No2008-09-022024-07-06US flag
US7462625No2008-12-092021-01-25US flag
US7179815No2007-02-202021-03-07US flag
US7056927No2006-06-062024-09-10US flag
US6872728No2005-03-292021-01-25US flag
US10881659No2021-01-052034-03-14US flag
US8058280No2011-11-152024-01-28US flag
US7300935No2007-11-272024-01-28US flag
US9346822No2016-05-242024-02-17US flag
US11033551No2021-06-152037-09-29US flag
US11045470No2021-06-292034-03-14US flag
US11459305No2008-11-072028-11-07US flag
US11542239No2019-07-232039-07-23US flag
US11690845No2020-08-272040-08-27US flag
US11793812No2018-05-032038-05-03US flag
US11795178No2013-09-272033-09-27US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)202-208CCanadian Jencycla label
Predicted Properties
PropertyValueSource
Water Solubility0.00668 mg/mLALOGPS
logP2.72ALOGPS
logP3.22Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)17.59Chemaxon
pKa (Strongest Basic)-1.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity87.42 m3·mol-1Chemaxon
Polarizability34.59 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9413
Caco-2 permeable+0.8572
P-glycoprotein substrateSubstrate0.6346
P-glycoprotein inhibitor IInhibitor0.5079
P-glycoprotein inhibitor IINon-inhibitor0.9087
Renal organic cation transporterNon-inhibitor0.7603
CYP450 2C9 substrateNon-substrate0.7759
CYP450 2D6 substrateNon-substrate0.9237
CYP450 3A4 substrateSubstrate0.7415
CYP450 1A2 substrateNon-inhibitor0.844
CYP450 2C9 inhibitorNon-inhibitor0.8688
CYP450 2D6 inhibitorNon-inhibitor0.9386
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8333
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7876
Ames testNon AMES toxic0.9319
CarcinogenicityNon-carcinogens0.9417
BiodegradationNot ready biodegradable0.9512
Rat acute toxicity1.8788 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8777
hERG inhibition (predictor II)Non-inhibitor0.7744
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.3 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00w9-0690000000-7050c3192b843aecc482
Mass Spectrum (Electron Ionization)MSsplash10-01rt-4950000000-fcbe8bf03b1aa103152b
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-0391000000-ae51cc90bb8f2161f149
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0j59-2494000000-76c71f96c07e87ef8962
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1910000000-f3f4bbf8cfe62ee9f76d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a5c-3900000000-4b2a5d95e4b6d50f16fc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00ea-0790000000-60d1a1a37c0ba98d6a4a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00e9-0890000000-5d3b8210450a1c43b119
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0391000000-ae51cc90bb8f2161f149
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ar0-3920000000-e31fa7c9e871f2e39846
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-4b5cdf64799888e5578a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-833867c2579583d501b8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-25ad08ac79cac4b824a2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-0790000000-a24afa7e0ac75a9c360d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xs-0390000000-b7c7c419fa214652fb38
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052b-0900000000-4329c825378100ff7f1d
1H NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-183.9978433
predicted
DarkChem Lite v0.1.0
[M-H]-182.9018433
predicted
DarkChem Lite v0.1.0
[M-H]-182.9171433
predicted
DarkChem Lite v0.1.0
[M-H]-173.74422
predicted
DeepCCS 1.0 (2019)
[M+H]+184.5141433
predicted
DarkChem Lite v0.1.0
[M+H]+183.6266433
predicted
DarkChem Lite v0.1.0
[M+H]+183.4477433
predicted
DarkChem Lite v0.1.0
[M+H]+175.70131
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.9629433
predicted
DarkChem Lite v0.1.0
[M+Na]+182.8139433
predicted
DarkChem Lite v0.1.0
[M+Na]+181.79655
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Progesterone receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
Gene Name
PGR
Uniprot ID
P06401
Uniprot Name
Progesterone receptor
Molecular Weight
98979.96 Da
References
  1. Garcia-Becerra R, Cooney AJ, Borja-Cacho E, Lemus AE, Perez-Palacios G, Larrea F: Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins. J Steroid Biochem Mol Biol. 2004 Jun;91(1-2):21-7. [Article]
  2. Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinal dehydrogenase activity
Specific Function
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid...
Gene Name
AKR1C4
Uniprot ID
P17516
Uniprot Name
Aldo-keto reductase family 1 member C4
Molecular Weight
37066.52 Da
References
  1. Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid delta-isomerase activity
Specific Function
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
Gene Name
HSD3B2
Uniprot ID
P26439
Uniprot Name
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
Molecular Weight
42051.845 Da
References
  1. Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Electron carrier activity
Specific Function
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...

Components:
References
  1. Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihyd...
Gene Name
AKR1D1
Uniprot ID
P51857
Uniprot Name
3-oxo-5-beta-steroid 4-dehydrogenase
Molecular Weight
37376.615 Da
References
  1. Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Lo Loestrin Fe oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
  2. FDA Approved Drug Products: Lo Loestrin Fe oral tablets [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Frohlich M, Albermann N, Sauer A, Walter-Sack I, Haefeli WE, Weiss J: In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem Pharmacol. 2004 Dec 15;68(12):2409-16. doi: 10.1016/j.bcp.2004.08.026. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48