BREMELANOTIDE ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C50H68N14O10.C2H4O2
Molecular Weight	1085.2147
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.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=MAYUSRUHXFWITM-GBRHMYBBSA-N

InChI=1S/C50H68N14O10.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t35-,36-,37-,38+,39-,40-,41-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C50H68N14O10
Molecular Weight	1025.1627
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.mdmag.com/medical-news/fda-accepts-bremelanotide-nda-for-treatment-of-hypoactive-sexual-desire-disorder | https://www.ncbi.nlm.nih.gov/pubmed/27181790 | https://progenpeptide.com/pt141.html

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

Primary Target	Pharmacology	Condition	Potency
Melanocortin receptor 4 5 Target ID: CHEMBL259 Sources: https://www.palatin.com/research-focus/female-sexual-dysfunction/what-is-bremelanotide/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210557s000lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/17584130	Agonist 2678
Melanocortin receptor 1 4 Target ID: CHEMBL3795 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210557s000lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/17584130	Agonist 2678
Melanocortin receptor 3 2 Target ID: CHEMBL4644 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17584130 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210557s000lbl.pdf	Agonist 2678

C_max

Value	Dose	Co-administered	Analyte	Population
72.8 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf	1.75 mg single, subcutaneous dose: 1.75 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		BREMELANOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
276 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf	1.75 mg single, subcutaneous dose: 1.75 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		BREMELANOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.7 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf	1.75 mg single, subcutaneous dose: 1.75 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		BREMELANOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
79% OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf	1.75 mg single, subcutaneous dose: 1.75 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:		BREMELANOTIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1.75 mg 10 times / 24 weeks multiple, subcutaneous Recommended Dose: 1.75 mg, 10 times / 24 weeks Route: subcutaneous Route: multiple Dose: 1.75 mg, 10 times / 24 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210557s000lbl.pdf	unhealthy, 19-56 years old n = 627 Health Status: unhealthy Condition: hypoactive sexual desire disorder Age Group: 19-56 years old Sex: F Population Size: 627 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210557s000lbl.pdf	Disc. AE: Nausea, Headache... Other AEs: Nausea, Flushing... AEs leading to discontinuation/dose reduction: Nausea (8%) Headache (2%) Vomiting (1%) Flushing (1%) Injection site reactions (1%) Flu-like symptoms (grade 1-2, <1%) Increased blood pressure (grade 1-2, <1%) Other AEs: Nausea (grade 1-2, 40%) Flushing (grade 1-2, 20.3%) Injection site reactions (grade 1-2, 13.2%) Headache (grade 1-2, 11.3%) Vomiting (grade 1-2, 4.8%) Cough (grade 1-2, 3.3%) Fatigue (grade 1-2, 3.2%) Hot flush (grade 1-2, 2.7%) Paraesthesia (grade 1-2, 2.6%) Dizziness (grade 1-2, 2.2%) Nasal congestion (grade 1-2, 2.1%) Upper abdominal pain (grade 1-2, <2%) Diarrhea (grade 1-2, <2%) Myalgia (grade 1-2, <2%) Arthralgia (grade 1-2, <2%) Pain (grade 1-2, <2%) Restless leg syndrome (grade 1-2, <2%) Rhinorrhea (grade 1-2, <2%) Creatine phosphokinase increased (grade 1-2, <2%) Blood pressure increased (grade 1-2, <2%) Pain in extremity (grade 1-2, <2%) Hyperpigmentation skin (grade 1-2, <2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210557s000lbl.pdf
20 mg 1 times / day single, intranasal Highest studied dose Dose: 20 mg, 1 times / day Route: intranasal Route: single Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14963471/	healthy, mean age 32.7 n = 24 Health Status: healthy Age Group: mean age 32.7 Sex: M Population Size: 24 Sources: https://pubmed.ncbi.nlm.nih.gov/14963471/	Other AEs: Flushing... Other AEs: Flushing (mild, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/14963471/
20 mg 1 times / day single, intranasal Highest studied dose Dose: 20 mg, 1 times / day Route: intranasal Route: single Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14963471/	healthy, mean age 32.7 n = 6 Health Status: healthy Age Group: mean age 32.7 Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/14963471/	Other AEs: Vomiting, Feeling hot... Other AEs: Vomiting (mild, 16.7%) Feeling hot (mild, 33.3%) Somnolence (mild, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/14963471/
1.75 mg 3 times / week multiple, subcutaneous Dose: 1.75 mg, 3 times / week Route: subcutaneous Route: multiple Dose: 1.75 mg, 3 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/31599840/	unhealthy, mean age 38.5 n = 627 Health Status: unhealthy Condition: hypoactive sexual desire disorder Age Group: mean age 38.5 Sex: F Population Size: 627 Sources: https://pubmed.ncbi.nlm.nih.gov/31599840/	Other AEs: Paresthesia, Injection site erythema... Other AEs: Paresthesia (grade 1-2, 2.6%) Injection site erythema (grade 1-2, 2.9%) Injection site pruritus (grade 1-2, 2.1%) Sources: https://pubmed.ncbi.nlm.nih.gov/31599840/
10 mg 1 times / day single, subcutaneous MTD Dose: 10 mg, 1 times / day Route: subcutaneous Route: single Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf	healthy n = 6 Health Status: healthy Sex: M Population Size: 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf	Other AEs: Vomiting... Other AEs: Vomiting (grade 1-2, 50%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 inducer 781	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882 CYP2B6 810 CYP2C8 911 OATP1B3 706 P-gp 1461 OAT3 642 BCRP 699 OAT1 599 OATP1B1 788 OCT2 647		CYP1A2 701 CYP2B6 547 CYP2C19 293

Drug as perpetrator

Target	Modality	Activity
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	low [Inhibition 1 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	low [Inhibition 1 uM]
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	low [Inhibition 1 uM]
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	low
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	low
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	low
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	low
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no [Inhibition 200 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 68;427	no [Ki 16 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no [Ki 35 uM]
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no
CYP2C19 1553	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=427 Page: 427.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=428 Page: 428.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/210557Orig1s000MultidisciplineR.pdf#page=395 Page: 395.0

Sourcing

Vendor/Aggregator	ID	URL
Acorn PharmaTech	ACN-057294	http://www.acornpharmatech.com/
BOC Sciences	189691-06-3	https://www.bocsci.com/bremelanotide-cas-189691-06-3-item-61871.html
BioSynth	Q-200747	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-200747.html
Chemenu	CM101686	http://www.chemenu.com/products/CM101686
Chemspace	CSSB02125551071	https://chem-space.com/CSSB02125551071
Hairui	BRCQ032	http://www.hairuichem.com/en/product/189691-06-3.html
MolPort	MolPort-009-194-183	https://www.molport.com/shop/molecule-link/MolPort-009-194-183
MuseChem	M043676	https://www.musechem.com/product/M043676.html
Smolecule	S522013	http://www.smolecule.com/products/s522013
THE BioTek	bt-261470	https://www.thebiotek.com/product/inhibitors/bt-261470
THE BioTek	bt-242583	https://www.thebiotek.com/product/peptides/bt-242583
eNovation Chemicals	D679352	https://www.enovationchem.com/ProductDetails.asp?ProductID=D679352
iChemical	EBD19124	http://www.ichemical.com/products/189691-06-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
PT-141: a melanocortin agonist for the treatment of sexual dysfunction.	2003 Jun	12851303
Bremelanotide for female sexual dysfunctions in premenopausal women: a randomized, placebo-controlled dose-finding trial.	2016 Jun	27181790
Re: Bremelanotide for Female Sexual Dysfunctions in Premenopausal Women: A Randomized, Placebo-Controlled Dose-Finding Trial.	2016 Nov	27751477
Phase I Randomized Placebo-controlled, Double-blind Study of the Safety and Tolerability of Bremelanotide Coadministered With Ethanol in Healthy Male and Female Participants.	2017 Mar	28189361

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:16:54 UTC 2023` Edited by `admin` on `Sat Dec 16 15:16:54 UTC 2023`
Record UNII	PV2WI7495P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BREMELANOTIDE ACETATE

Official Name

English

PT-141

Code

English

L-LYSINE, N-ACETYL-L-NORLEUCYL-L-.ALPHA.-ASPARTYL-L-HISTIDYL-D-PHENYLALANYL-L-ARGINYL-L-TRYPTOPHYL-, (2->7)-LACTAM, ACETIC ACID (1:1)

Systematic Name

English

BREMELANOTIDE ACETATE [USAN]

Common Name

English

VYLEESI

Brand Name

English

BREMELANOTIDE ACETATE [MI]

Common Name

English

BREMELANOTIDE ACETATE [ORANGE BOOK]

Common Name

English

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

Systematic Name

English

Bremelanotide acetate [WHO-DD]

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C171917