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Also known as: 151272-78-5, D19v7048jk, Ep 24332, Ep-24332, Ac-d-nal-d-cpa-d-pal-ser-tyr-d-hci-leu-lys(ipr)-pro-d-ala-nh2, D-alaninamide, n-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n6-(aminocarbonyl)-d-lysyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-

Molecular Formula

C₇₄H₁₀₀ClN₁₅O₁₄

Molecular Weight

1459.1 g/mol

InChI Key

NOENHWMKHNSHGX-IAOPALDYSA-N

FDA UNII

D19V7048JK

Teverelix is a synthetic decapeptide and antagonist of the naturally occurring gonadotropin-releasing hormone (GnRH), with potential hormone production inhibitory and antineoplastic activities. Upon administration, teverelix directly competes with GnRH for receptor binding in the anterior pituitary gland, thereby inhibiting GnRH receptor signaling. This inhibits the secretion and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone. Since testosterone is required to sustain prostate growth, reducing testosterone levels may inhibit hormone-dependent prostate cancer cell proliferation. In females, this prevents the production of estrogen by the ovaries and may relieve symptoms from sex-hormone dependent diseases.

1 2D Structure

Teverelix

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-(carbamoylamino)hexanoyl]amino]-4-methylpentanoyl]amino]-6-(propan-2-ylamino)hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C74H100ClN15O14/c1-43(2)35-57(66(96)84-56(19-10-11-32-79-44(3)4)73(103)90-34-14-20-63(90)72(102)81-45(5)64(76)94)85-65(95)55(18-9-12-33-80-74(77)104)83-68(98)59(38-48-24-29-54(93)30-25-48)88-71(101)62(42-91)89-70(100)61(40-50-15-13-31-78-41-50)87-69(99)60(37-47-22-27-53(75)28-23-47)86-67(97)58(82-46(6)92)39-49-21-26-51-16-7-8-17-52(51)36-49/h7-8,13,15-17,21-31,36,41,43-45,55-63,79,91,93H,9-12,14,18-20,32-35,37-40,42H2,1-6H3,(H2,76,94)(H,81,102)(H,82,92)(H,83,98)(H,84,96)(H,85,95)(H,86,97)(H,87,99)(H,88,101)(H,89,100)(H3,77,80,104)/t45-,55-,56+,57+,58-,59+,60-,61-,62+,63+/m1/s1

2.1.3 InChI Key

NOENHWMKHNSHGX-IAOPALDYSA-N

2.2 Other Identifiers

2.2.1 UNII

D19V7048JK

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ep 24332

2. Ep-24332

2.3.2 Depositor-Supplied Synonyms

1. 151272-78-5

2. D19v7048jk

3. Ep 24332

4. Ep-24332

5. Ac-d-nal-d-cpa-d-pal-ser-tyr-d-hci-leu-lys(ipr)-pro-d-ala-nh2

6. D-alaninamide, N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n6-(aminocarbonyl)-d-lysyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-

7. D-23234

8. Teverelixum

9. Refchem:188970

10. (2s)-1-((2s)-2-(((2s)-2-(((2r)-2-(((2s)-2-(((2s)-2-(((2r)-2-(((2r)-2-(((2r)-2-acetamido-3-naphthalen-2-ylpropanoyl)amino)-3-(4-chlorophenyl)propanoyl)amino)-3-pyridin-3-ylpropanoyl)amino)-3-hydroxypropanoyl)amino)-3-(4-hydroxyphenyl)propanoyl)amino)-6-(carbamoylamino)hexanoyl)amino)-4-methylpentanoyl)amino)-6-(propan-2-ylamino)hexanoyl)-n-((2r)-1-amino-1-oxopropan-2-yl)pyrrolidine-2-carboxamide

11. Teverelix [inn]

12. Unii-d19v7048jk

13. D 23234

14. Orb1699148

15. Dtxsid301033772

16. N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-l-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n6-(aminocarbonyl)-d-lysyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-d-alaninamide

17. Akos040749635

18. Db05624

19. Hy-105173

20. Cs-0025196

21. Q27275967

22. N-acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-n6-(aminocarbonyl)-d-lysyl-l-leucyl-n6-(1-methylethyl)-l-lysyl-l-prolyl-d-alaninamide

23. N-acetyl-3-(2-naphthyl)-d-alanyl-p-chloro-d-phenylalanyl-3-(3-pyridyl)-d-alanyl-l-seryl-l-tyrosyl-n(sup 6)-carbamoyl-d-lysyl-l-leucyl-n(sup 6)-isopropyl-l-lysyl-l-prolyl-d-alaninamide

2.4 Create Date

2007-07-04

3 Chemical and Physical Properties

Molecular Formula	C₇₄H₁₀₀ClN₁₅O₁₄
Molecular Weight	1459.1 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	15
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	41
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	446
Heavy Atom Count	104
Formal Charge	0
Complexity	2810
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in benign prostatic hyperplasia, endometriosis, and prostate cancer.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Hormone Antagonists

Chemical substances which inhibit the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.

5.2 Mechanism of Action

Teverelix is a GnRH (Gonadotropin releasing hormone) antagonist.

Drugs in Development

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