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Also known as: 97048-13-0, 146479-72-3, 1-[19-amino-7-(2-amino-2-oxoethyl)-13-butan-2-yl-10-(1-hydroxyethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide, Fertinex; fertinorm; metrodin; orgafol; urofollitrophin, 26995-91-5, Schembl19712185

Molecular Formula

C₄₂H₆₅N₁₁O₁₂S₂

Molecular Weight

980.2 g/mol

InChI Key

ZDRRIRUAESZNIH-UHFFFAOYSA-N

A protein extract of human menopausal urine in which LUTEINIZING HORMONE has been partially or completely removed. Urofollitropin represents FOLLICLE STIMULATING HORMONE from the urine.

1 2D Structure

Follistim

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[19-amino-7-(2-amino-2-oxoethyl)-13-butan-2-yl-10-(1-hydroxyethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C42H65N11O12S2/c1-6-21(4)33-40(63)52-34(22(5)54)41(64)49-28(16-31(44)56)37(60)50-29(19-67-66-18-25(43)35(58)47-27(38(61)51-33)15-23-9-11-24(55)12-10-23)42(65)53-13-7-8-30(53)39(62)48-26(14-20(2)3)36(59)46-17-32(45)57/h9-12,20-22,25-30,33-34,54-55H,6-8,13-19,43H2,1-5H3,(H2,44,56)(H2,45,57)(H,46,59)(H,47,58)(H,48,62)(H,49,64)(H,50,60)(H,51,61)(H,52,63)

2.1.3 InChI Key

ZDRRIRUAESZNIH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSSCC(C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O)N)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)C(C)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Bravelle

2. Fertinex

3. Follicle Stimulating Hormone, Human Urine

4. Follicle-stimulating Hormone, Human Urine

5. Follitrin

6. High Purity, Metrodin

7. Human Fsh, Urinary

8. Metrodin

9. Metrodin High Purity

10. Metrodin Hp

11. Neo Fertinorm

12. Urinary Human Fsh

2.2.2 Depositor-Supplied Synonyms

1. 97048-13-0

2. 146479-72-3

3. 1-[19-amino-7-(2-amino-2-oxoethyl)-13-butan-2-yl-10-(1-hydroxyethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

4. Fertinex; Fertinorm; Metrodin; Orgafol; Urofollitrophin

5. 26995-91-5

6. Schembl19712185

7. Dtxsid10869286

8. Q4006490

9. 1-{19-amino-7-(2-amino-2-oxoethyl)-13-(butan-2-yl)-10-(1-hydroxyethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl}prolylleucylglycinamide

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₄₂H₆₅N₁₁O₁₂S₂
Molecular Weight	980.2 g/mol
XLogP3	-1.5
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	15
Exact Mass	979.42555890 g/mol
Monoisotopic Mass	979.42555890 g/mol
Topological Polar Surface Area	427 Å²
Heavy Atom Count	67
Formal Charge	0
Complexity	1790
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	10
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For treatment of female infertility

FDA Label

Treatment of hypogonadotrophic hypogonadism, Treatment of female infertility

5 Pharmacology and Biochemistry

5.1 Pharmacology

Used for the treatment of female infertility, urofollitropin or follicle stimulating hormone (FSH) stimulates ovarian follicular growth in women who do not have primary ovarian failure. FSH, the active component of urofollitropin is the primary hormone responsible for follicular recruitment and development.

5.2 ATC Code

G - Genito urinary system and sex hormones

G03 - Sex hormones and modulators of the genital system

G03G - Gonadotropins and other ovulation stimulants

G03GA - Gonadotropins

G03GA04 - Urofollitropin

5.3 Absorption, Distribution and Excretion

Absorption

74%

Route of Elimination

Via liver and kidneys

Volume of Distribution

Time to peak in plasma: IM: 17 hours (single dose), 11 hours (multiple doses) SubQ: 21 hours (single dose), 10 hours (multiple doses)

5.4 Biological Half-Life

Circulation half life of 3-4 hours, elimination half life of 35-40 hours

5.5 Mechanism of Action

FSH binds to the follicle stimulating hormone receptor which is a G-coupled transmembrane receptor. Binding of the FSH to its receptor seems to induce phosphorylation and activation of the PI3K (Phosphatidylinositol-3-kinase) and Akt signaling pathway, which is known to regulate many other metabolic and related survival/maturation functions in cells.

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