Flibanserin
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MedKoo CAT#: 317112

CAS#: 167933-07-5

Description: Flibanserin is a full agonist of the 5-HT1A receptor (Ki = 1 nM) and, with lower affinity, as an antagonist of the 5-HT2A receptor (Ki = 49 nM) and antagonist or very weak partial agonist of the D4 receptor (Ki = 4–24 nM). Despite the much greater affinity of flibanserin for the 5-HT1A receptor, and for reasons that are unknown, flibanserin occupies the 5-HT1A and 5-HT2A receptors in vivo with similar percentages. Flibanserin also has low affinity for the 5-HT2B receptor (Ki = 89.3 nM) and the 5-HT2C receptor (Ki = 88.3 nM), both of which it behaves as an antagonist of. Flibanserin preferentially activates 5-HT1A receptors in the prefrontal cortex, demonstrating regional selectivity, and has been found to increase dopamine and norepinephrine levels and decrease serotonin levels in the rat prefrontal cortex, actions that were determined to be mediated by activation of the 5-HT1A receptor.[12] As such, flibanserin has been described as a norepinephrine-dopamine disinhibitor (NDDI). Flibanserin was approved in August 2015 for the treatment of pre-menopausal women with hypoactive sexual desire disorder (HSDD).


Chemical Structure

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Flibanserin
CAS# 167933-07-5

Theoretical Analysis

MedKoo Cat#: 317112
Name: Flibanserin
CAS#: 167933-07-5
Chemical Formula: C20H21F3N4O
Exact Mass: 390.16675
Molecular Weight: 390.41
Elemental Analysis: C, 61.53; H, 5.42; F, 14.60; N, 14.35; O, 4.10

Size Price Shipping out time Quantity
5mg USD 195 2 Weeks
10mg USD 335 2 Weeks
25mg USD 619 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-04. Prices are subject to change without notice.

Flibanserin is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: BIMT 17; BIMT-17; BIMT17; BIMT 17BS; BIMT-17BS; BIMT17BS; EBD6396; EBD 6396; EBD-6396; Flibanserin. Brand name: Addyi.

IUPAC/Chemical Name: 1-(2-{4-[3-(Trifluoromethyl)phenyl]piperazin-1-yl}ethyl)-1,3-dihydro-2H-benzimidazol-2-one

InChi Key: PPRRDFIXUUSXRA-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H21F3N4O/c21-20(22,23)15-4-3-5-16(14-15)26-11-8-25(9-12-26)10-13-27-18-7-2-1-6-17(18)24-19(27)28/h1-7,14H,8-13H2,(H,24,28)

SMILES Code: O=C1NC2=CC=CC=C2N1CCN3CCN(C4=CC=CC(C(F)(F)F)=C4)CC3

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 390.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Simon JA, Clayton AH, Parish SJ, Apfel SC, Millheiser L. Effects of Alcohol Administered With Flibanserin in Healthy Premenopausal Women: A Randomized, Double-Blind, Single-Dose Crossover Study. J Sex Med. 2019 Nov 14. pii: S1743-6095(19)31459-6. doi: 10.1016/j.jsxm.2019.10.004. [Epub ahead of print] PubMed PMID: 31735618.

2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548074/ PubMed PMID: 31643404.

3: Dean L. Flibanserin Therapy and CYP2C19 Genotype. 2019 Sep 23. In: Pratt V, McLeod H, Rubinstein W, Dean L, Kattman B, Malheiro A, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK546788/ PubMed PMID: 31550099.

4: Simon JA, Clayton AH, Kingsberg SA, Parish SJ, Kim NN, Millheiser L. Effects of Timing of Flibanserin Administration Relative to Alcohol Intake in Healthy Premenopausal Women: A Randomized, Double-Blind, Crossover Study. J Sex Med. 2019 Nov;16(11):1779-1786. doi: 10.1016/j.jsxm.2019.08.006. Epub 2019 Sep 12. PubMed PMID: 31522985.

5: Millheiser L, Clayton AH, Parish SJ, Kingsberg SA, Kim NN, Simon JA. Safety and Tolerability of Evening Ethanol Consumption and Bedtime Administration of Flibanserin in Healthy Premenopausal Female Subjects. Sex Med. 2019 Dec;7(4):418-424. doi: 10.1016/j.esxm.2019.08.003. Epub 2019 Sep 10. PubMed PMID: 31519497.

6: Ahmed RM, Abdallah IA. Determination of flibanserin in the presence of confirmed degradation products by a third derivative emission spectrofluorometric method: Application to pharmaceutical formulation. Spectrochim Acta A Mol Biomol Spectrosc. 2019 Aug 26;225:117491. doi: 10.1016/j.saa.2019.117491. [Epub ahead of print] PubMed PMID: 31476647.

7: He L, You W, Wang S, Jiang T, Chen C. A rapid and sensitive UPLC-MS/MS method for the determination of flibanserin in rat plasma: application to a pharmacokinetic study. BMC Chem. 2019 Aug 27;13(1):111. doi: 10.1186/s13065-019-0620-9. eCollection 2019 Dec. PubMed PMID: 31463480; PubMed Central PMCID: PMC6710871.

8: Simon JA, Kingsberg SA, Goldstein I, Kim NN, Hakim B, Millheiser L. Weight Loss in Women Taking Flibanserin for Hypoactive Sexual Desire Disorder (HSDD): Insights Into Potential Mechanisms. Sex Med Rev. 2019 Oct;7(4):575-586. doi: 10.1016/j.sxmr.2019.04.003. Epub 2019 Jun 10. Review. PubMed PMID: 31196764.

9: Sultan MA, El-Eryan RT, Attia AK, Eissa MJ. Development and validation of liquid chromatography-electrospray-tandem mass spectrometry method for determination of flibanserin in human plasma: Application to pharmacokinetic study on healthy female volunteers. Biomed Chromatogr. 2019 Aug;33(8):e4545. doi: 10.1002/bmc.4545. Epub 2019 May 6. PubMed PMID: 30937940.

10: Kingsberg SA, McElroy SL, Clayton AH. Evaluation of Flibanserin Safety: Comparison with Other Serotonergic Medications. Sex Med Rev. 2019 Jul;7(3):380-392. doi: 10.1016/j.sxmr.2018.12.003. Epub 2019 Feb 22. Review. PubMed PMID: 30803922.

11: Simon JA, Thorp J, Millheiser L. Flibanserin for Premenopausal Hypoactive Sexual Desire Disorder: Pooled Analysis of Clinical Trials. J Womens Health (Larchmt). 2019 Jun;28(6):769-777. doi: 10.1089/jwh.2018.7516. Epub 2019 Feb 1. PubMed PMID: 30707049.

12: Baid R, Agarwal R. Flibanserin: A controversial drug for female hypoactive sexual desire disorder. Ind Psychiatry J. 2018 Jan-Jun;27(1):154-157. doi: 10.4103/ipj.ipj_20_16. PubMed PMID: 30416308; PubMed Central PMCID: PMC6198608.

13: Shingare RD, Kulkarni AS, Sutar RL, Reddy DS. Route to Benzimidazol-2-ones via Decarbonylative Ring Contraction of Quinoxalinediones: Application to the Synthesis of Flibanserin, A Drug for Treating Hypoactive Sexual Desire Disorder in Women and Marine Natural Product Hunanamycin Analogue. ACS Omega. 2017 Aug 31;2(8):5137-5141. doi: 10.1021/acsomega.7b00819. Epub 2017 Aug 29. PubMed PMID: 30023739; PubMed Central PMCID: PMC6044990.

14: Segal JZ. Sex, drugs, and rhetoric: The case of flibanserin for 'female sexual dysfunction'. Soc Stud Sci. 2018 Aug;48(4):459-482. doi: 10.1177/0306312718778802. Epub 2018 Jun 3. PubMed PMID: 29862892.

15: Clements JN, Thompson B. Flibanserin for hypoactive sexual desire disorder in premenopausal women. JAAPA. 2018 Jun;31(6):51-53. doi: 10.1097/01.JAA.0000532129.61154.3e. PubMed PMID: 29846316.

16: Iqbal M, Ezzeldin E, Rezk NL, Bajrai AA, Al-Rashood KA. A validated UPLC-MS/MS method for flibanserin in plasma and its pharmacokinetic interaction with bosentan in rats. Bioanalysis. 2018 Jul;10(14):1087-1097. doi: 10.4155/bio-2018-0065. Epub 2018 Apr 25. PubMed PMID: 29692180.

17: Simon JA, Derogatis L, Portman D, Brown L, Yuan J, Kissling R. Flibanserin for Hypoactive Sexual Desire Disorder: An Open-Label Safety Study. J Sex Med. 2018 Mar;15(3):387-395. doi: 10.1016/j.jsxm.2017.12.016. PubMed PMID: 29502984.

18: Nappi RE, Cucinella L, Tiranini L, Martini E. Has flibanserin revolutionized the treatment of hypoactive sexual desire disorder or is there still room for more effective therapeutics? Expert Opin Pharmacother. 2018 Apr;19(5):421-423. doi: 10.1080/14656566.2018.1444751. Epub 2018 Feb 28. PubMed PMID: 29488405.

19: Anderson R, Moffatt CE. Ignorance Is Not Bliss: If We Don't Understand Hypoactive Sexual Desire Disorder, How Can Flibanserin Treat It? Commentary. J Sex Med. 2018 Mar;15(3):273-283. doi: 10.1016/j.jsxm.2018.01.001. Epub 2018 Feb 1. Review. PubMed PMID: 29396022.

20: Clayton AH, Croft HA, Yuan J, Brown L, Kissling R. Safety of Flibanserin in Women Treated With Antidepressants: A Randomized, Placebo-Controlled Study. J Sex Med. 2018 Jan;15(1):43-51. doi: 10.1016/j.jsxm.2017.11.005. PubMed PMID: 29289374.