BREMELANOTIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C50H68N14O10
Molecular Weight	1025.1647
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCC[C@H](NC(C)=O)C(=O)N[C@H]1CC(=O)NCCCC[C@H](NC(=O)[C@H](CC2=CNC3=CC=CC=C23)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](CC4=CC=CC=C4)NC(=O)[C@H](CC5=CN=CN5)NC1=O)C(O)=O

InChI

InChIKey=FFHBJDQSGDNCIV-MFVUMRCOSA-N

InChI=1S/C50H68N14O10/c1-3-4-16-35(58-29(2)65)43(67)64-41-25-42(66)54-20-11-10-18-37(49(73)74)60-46(70)39(23-31-26-56-34-17-9-8-15-33(31)34)62-44(68)36(19-12-21-55-50(51)52)59-45(69)38(22-30-13-6-5-7-14-30)61-47(71)40(63-48(41)72)24-32-27-53-28-57-32/h5-9,13-15,17,26-28,35-41,56H,3-4,10-12,16,18-25H2,1-2H3,(H,53,57)(H,54,66)(H,58,65)(H,59,69)(H,60,70)(H,61,71)(H,62,68)(H,63,72)(H,64,67)(H,73,74)(H4,51,52,55)/t35-,36-,37-,38+,39-,40-,41-/m0/s1

HIDE SMILES / InChI

Description

Bremelanotide (formerly PT-141) was developed for the treatment of female sexual dysfunction, hemorrhagic shock, and reperfusion injury. Bremelanotide, a synthetic peptide analog of α-melanocyte-stimulating hormone (α-MSH) is an agonist at melanocortin receptors including the MC3R and MC4R, which are expressed primarily in the central nervous system. Bremelanotide originally was tested for intranasal administration in treating female sexual dysfunction but this application was temporarily discontinued in 2008 after concerns were raised over adverse side effects of increased blood pressure. It appears that development for hemorrhagic shock and reperfusion injury has been discontinued. Palatin Technologies licensed North American development and commercialization rights of bremelanotide to Amag in January 2017. In June 2018, the US Food and Drug Administration (FDA) accepted AMAG Pharmaceuticals’ new drug application for bremelanotide for treatment of hypoactive sexual desire disorder in premenopausal women. If approved, bremelanotide will be available as a self-administered, disposable subcutaneous auto-injector used in anticipation of a sexual encounter.

Originator

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
Melanocortin receptor 4 8	Agonist 2,752
Melanocortin receptor 1 4	Agonist 2,752
Melanocortin receptor 3 2	Agonist 2,752

C_max

Value	Dose	Co-administered	Analyte	Population
72.8 ng/mL	1.75 mg single, subcutaneous		BREMELANOTIDE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
276 ng × h/mL	1.75 mg single, subcutaneous		BREMELANOTIDE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.7 h	1.75 mg single, subcutaneous		BREMELANOTIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
79%	1.75 mg single, subcutaneous		BREMELANOTIDE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1.75 mg 10 times / 24 weeks multiple, subcutaneous Recommended	unhealthy, 19-56 years old	Disc. AE: Nausea, Headache... Other AEs: Nausea, Flushing...
20 mg 1 times / day single, intranasal Highest studied dose	healthy, mean age 32.7	Other AEs: Flushing...
20 mg 1 times / day single, intranasal Highest studied dose	healthy, mean age 32.7	Other AEs: Vomiting, Feeling hot...
1.75 mg 3 times / week multiple, subcutaneous	unhealthy, mean age 38.5	Other AEs: Paresthesia, Injection site erythema...
10 mg 1 times / day single, subcutaneous MTD	healthy	Other AEs: Vomiting...

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AEs

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AE	Significance	Dose	Population
Flushing	1% Disc. AE	1.75 mg 10 times / 24 weeks multiple, subcutaneous Recommended	unhealthy, 19-56 years old
Injection site reactions	1% Disc. AE	1.75 mg 10 times / 24 weeks multiple, subcutaneous Recommended	unhealthy, 19-56 years old
Vomiting	1% Disc. AE	1.75 mg 10 times / 24 weeks multiple, subcutaneous Recommended	unhealthy, 19-56 years old
Headache	2% Disc. AE	1.75 mg 10 times / 24 weeks multiple, subcutaneous Recommended	unhealthy, 19-56 years old
Nausea	8% Disc. AE	1.75 mg 10 times / 24 weeks multiple, subcutaneous Recommended	unhealthy, 19-56 years old

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 inducer 1,087	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2A6 879 CYP2C19 2,057 CYP2E1 1,060 CYP2B6 926 CYP2C8 1,057 OATP1B3 961 P-gp 1,741 OAT3 747 BCRP 910 OAT1 725 OATP1B1 1,079 OCT2 779		CYP1A2 832 CYP2B6 669 CYP2C19 329

Drug as perpetrator

Show entries

Target	Modality	Activity
OAT3 749	inhibitor 4,027	low [Inhibition 1 uM]
OATP1B3 970	inhibitor 4,027	low [Inhibition 1 uM]
P-gp 1,932	inhibitor 4,027	low [Inhibition 1 uM]
BCRP 985	inhibitor 4,027	low
OAT1 730	inhibitor 4,027	low

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
Acorn PharmaTech	ACN-057294	http://www.acornpharmatech.com/
BioSynth	Q-200747	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-200747.html
BOC Sciences	189691-06-3	https://www.bocsci.com/bremelanotide-cas-189691-06-3-item-61871.html
Chemenu	CM101686	http://www.chemenu.com/products/CM101686
Chemspace	CSSB02125551071	https://chem-space.com/CSSB02125551071

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PubMed

PubMed

Title	Date	PubMed
PT-141: a melanocortin agonist for the treatment of sexual dysfunction.	2003 Jun	12851303

Sample Use Guides

In Vivo Use Guide

Subjects will self-administer a fixed dose of bremelanotide (BMT) subcutaneously (SC) via auto-injector on an as needed basis with no more than 1 dose taken every 24 hours.

Route of Administration: Other

Show entries

Name

Type

Language

PT-141 FREE BASE

Preferred Name

English

BREMELANOTIDE

Official Name

English

N-ACETYL-L-2-AMINOHEXANOYL-L-.ALPHA.-ASPARTYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-L-LYSINE-(2->7)-LACTAM

Common Name

English

bremelanotide [INN]

Common Name

English

L-LYSINE, N-ACETYL-L-NORLEUCYL-L-.ALPHA.-ASPARTYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-, (2->7)-LACTAM

Common Name

English

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Classification Tree

Code System

Code

Peptides

WIKIPEDIA

Designer-drugs-Bremelanotide

Hormone Therapy Agent

NCI_THESAURUS

C548

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Code System

Code

Type

Description

CAS

189691-06-3

PRIMARY

MERCK INDEX

m12151

PRIMARY

FDA UNII

6Y24O4F92S

PRIMARY

ChEMBL

CHEMBL2070241

PRIMARY

MESH

C476721

PRIMARY

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ACTIVE MOIETY


					6Y24O4F92S

BREMELANOTIDE

SALT/SOLVATE (PARENT)


					PV2WI7495P

BREMELANOTIDE ACETATE

SMILES

InChI

Originator

Approval Year

Targets

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Tox targets

Sourcing

PubMed

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator