Quinagolide hydrochloride
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MedKoo CAT#: 202390

CAS#: 94424-50-7 (HCl)

Description: Quinagolide is a selective, D2 receptor agonist (or prolactin-release inhibitor) that is used for the treatment of elevated levels of prolactin. Quinagolide (Norprolac) was approved in European Community, but not in USA as of December, 2011. Quinagolide prevents the production of a chemical called prolactin. Prolactin is involved in many processes within the body, such as milk production after childbirth and altering levels of hormones involved with controlling the menstrual cycle and fertility. Quinagolide is therefore helpful in reducing prolactin levels to reduce milk production for certain medical reasons and to treat some types of infertility, breast problems and menstrual disorders.

Chemical Structure

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Quinagolide hydrochloride
CAS# 94424-50-7 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202390
Name: Quinagolide hydrochloride
CAS#: 94424-50-7 (HCl)
Chemical Formula: C20H34ClN3O3S
Exact Mass: 0.00
Molecular Weight: 432.020
Elemental Analysis: C, 55.60; H, 7.93; Cl, 8.21; N, 9.73; O, 11.11; S, 7.42

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Related CAS #: 94424-50-7 (HCl)   87056-78-8 (free base)    

Synonym: BRN-6074559; BRN6074559; BRN 6074559; CV205502; CV-205502; CV 205502; Quinagolide, Quinagolide HCl; Quinagolide hydrochloride trade name: NORPROLAC.

IUPAC/Chemical Name: ( 3S,4aS,10aR)-3-(diethylsulfamoylamino)-6-hydroxy-1-propyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinoline hydrochloride

InChi Key: DVLKVIJLALMCBQ-MSSRUXLCSA-N

InChi Code: InChI=1S/C20H33N3O3S.ClH/c1-4-10-22-14-17(21-27(25,26)23(5-2)6-3)11-16-12-18-15(13-19(16)22)8-7-9-20(18)24;/h7-9,16-17,19,21,24H,4-6,10-14H2,1-3H3;1H/t16-,17+,19-;/m1./s1

SMILES Code: CCCN1C[C@@H](NS(=O)(N(CC)CC)=O)C[C@]2([H])CC3=C(O)C=CC=C3C[C@@]12[H].[H]Cl

Appearance: white 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

More Info: Related CAS# 94424-50-7 (HCl); 87056-78-8 (free base)

Biological target: Quinagolide hydrochloride (CV205-502 hydrochloride) is a selective and orally active dopamine D2 receptor agonist. Quinagolide hydrochloride is an inhibitor of prolactin. Quinagolide hydrochloride down-regulates AKT levels and its phosphorylation. Quinagolide hydrochloride shows antitumor effects, it can be used for the research of cancer.
In vitro activity: This study isolated E-MSCs from eutopic endometrial tissue and from ovarian and peritoneal endometriotic lesions and tested the effect of quinagolide on their proliferation and matrix invasion ability. Quinagolide inhibited the invasive properties of E-MSCs, but not their proliferation, and limited their endothelial differentiation. Together with the reported effects on endometrial and endothelial cells, the observed inhibition of E-MSCs may increase the rationale for quinagolide in endometriosis treatment. Reference: Int J Mol Sci. 2022 Feb 4;23(3):1775. https://pubmed.ncbi.nlm.nih.gov/35163699/
In vivo activity: Dopamine agonists (DAs), including quinagolide, downregulated proangiogenic and upregulatde antiangiogenic pathways in inflammatory, endothelial and endometrial cells, blocking cellular proliferation and reducing lesion size and pain in woman subjects. The findings of this study support the use of DAs in the medical management of endometriosis while maintaining ovulation. A combined approach of DAs and pentoxifylline may be a smart and novel method of targeting endometriosis. Reference: Hum Reprod. 2021 Mar 18;36(4):850-858. https://pubmed.ncbi.nlm.nih.gov/33355352/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 3.9 8.91

Preparing Stock Solutions

The following data is based on the product molecular weight 432.02 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.

Recalculate based on batch purity %
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
Formulation protocol: 1. Iampietro C, Brossa A, Canosa S, Tritta S, Croston GE, Reinheimer TM, Bonelli F, Carosso AR, Gennarelli G, Cosma S, Benedetto C, Revelli A, Bussolati B. Quinagolide Treatment Reduces Invasive and Angiogenic Properties of Endometrial Mesenchymal Stromal Cells. Int J Mol Sci. 2022 Feb 4;23(3):1775. doi: 10.3390/ijms23031775. PMID: 35163699; PMCID: PMC8836593. 2. Jaquet P, Ouafik L, Saveanu A, Gunz G, Fina F, Dufour H, Culler MD, Moreau JP, Enjalbert A. Quantitative and functional expression of somatostatin receptor subtypes in human prolactinomas. J Clin Endocrinol Metab. 1999 Sep;84(9):3268-76. doi: 10.1210/jcem.84.9.5962. PMID: 10487698. 3. Morange I, Barlier A, Pellegrini I, Brue T, Enjalbert A, Jaquet P. Prolactinomas resistant to bromocriptine: long-term efficacy of quinagolide and outcome of pregnancy. Eur J Endocrinol. 1996 Oct;135(4):413-20. doi: 10.1530/eje.0.1350413. PMID: 8921822. 4. Pellicer N, Galliano D, Herraiz S, Bagger YZ, Arce JC, Pellicer A. Use of dopamine agonists to target angiogenesis in women with endometriosis. Hum Reprod. 2021 Mar 18;36(4):850-858. doi: 10.1093/humrep/deaa337. PMID: 33355352.
In vitro protocol: 1. Iampietro C, Brossa A, Canosa S, Tritta S, Croston GE, Reinheimer TM, Bonelli F, Carosso AR, Gennarelli G, Cosma S, Benedetto C, Revelli A, Bussolati B. Quinagolide Treatment Reduces Invasive and Angiogenic Properties of Endometrial Mesenchymal Stromal Cells. Int J Mol Sci. 2022 Feb 4;23(3):1775. doi: 10.3390/ijms23031775. PMID: 35163699; PMCID: PMC8836593. 2. Jaquet P, Ouafik L, Saveanu A, Gunz G, Fina F, Dufour H, Culler MD, Moreau JP, Enjalbert A. Quantitative and functional expression of somatostatin receptor subtypes in human prolactinomas. J Clin Endocrinol Metab. 1999 Sep;84(9):3268-76. doi: 10.1210/jcem.84.9.5962. PMID: 10487698.
In vivo protocol: 1. Morange I, Barlier A, Pellegrini I, Brue T, Enjalbert A, Jaquet P. Prolactinomas resistant to bromocriptine: long-term efficacy of quinagolide and outcome of pregnancy. Eur J Endocrinol. 1996 Oct;135(4):413-20. doi: 10.1530/eje.0.1350413. PMID: 8921822. 2. Pellicer N, Galliano D, Herraiz S, Bagger YZ, Arce JC, Pellicer A. Use of dopamine agonists to target angiogenesis in women with endometriosis. Hum Reprod. 2021 Mar 18;36(4):850-858. doi: 10.1093/humrep/deaa337. PMID: 33355352.

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1: Boutinaud M, Lollivier V, Finot L, Bruckmaier RM, Lacasse P. Mammary cell activity and turnover in dairy cows treated with the prolactin-release inhibitor quinagolide and milked once daily. J Dairy Sci. 2012 Jan;95(1):177-87. doi: 10.3168/jds.2011-4461. PubMed PMID: 22192196.

2: Broekhof R, Gosselink MJ, Pijl H, Giltay EJ. The effect of aripiprazole and quinagolide, a dopamine agonist, in a patient with symptomatic pituitary prolactinoma and chronic psychosis. Gen Hosp Psychiatry. 2012 Mar-Apr;34(2):209.e1-3. doi: 10.1016/j.genhosppsych.2011.07.004. Epub 2011 Aug 26. PubMed PMID: 21872335.

3: Lacasse P, Lollivier V, Bruckmaier RM, Boisclair YR, Wagner GF, Boutinaud M. Effect of the prolactin-release inhibitor quinagolide on lactating dairy cows. J Dairy Sci. 2011 Mar;94(3):1302-9. doi: 10.3168/jds.2010-3649. PubMed PMID: 21338795.

4: Gómez R, Abad A, Delgado F, Tamarit S, Simón C, Pellicer A. Effects of hyperprolactinemia treatment with the dopamine agonist quinagolide on endometriotic lesions in patients with endometriosis-associated hyperprolactinemia. Fertil Steril. 2011 Mar 1;95(3):882-8.e1. doi: 10.1016/j.fertnstert.2010.10.024. Epub 2010 Nov 5. PubMed PMID: 21055747.

5: Lakatos G, Szücs N, Kender Z, Czirják S, Rácz K. [Macroprolactinemia associated with pituitary macroadenoma: treatment with quinagolide]. Orv Hetil. 2010 Jun 27;151(26):1072-5. doi: 10.1556/OH.2010.28896. Hungarian. PubMed PMID: 20558354.

6: Busso C, Fernández-Sánchez M, García-Velasco JA, Landeras J, Ballesteros A, Muñoz E, González S, Simón C, Arce JC, Pellicer A. The non-ergot derived dopamine agonist quinagolide in prevention of early ovarian hyperstimulation syndrome in IVF patients: a randomized, double-blind, placebo-controlled trial. Hum Reprod. 2010 Apr;25(4):995-1004. doi: 10.1093/humrep/deq005. Epub 2010 Feb 6. PubMed PMID: 20139430; PubMed Central PMCID: PMC2839910.

7: Vinkers DJ, van der Wee NJ. A case of mania after long-term use of quinagolide. Gen Hosp Psychiatry. 2007 Sep-Oct;29(5):464. PubMed PMID: 17888817.

8: Hrycek A, Pochopień-Kenig G, Scieszka J. Selected acute phase proteins and interleukin-6 in systemic lupus erythematosus patients treated with low doses of quinagolide. Autoimmunity. 2007 May;40(3):217-22. PubMed PMID: 17453721.

9: Hrycek A, Kusmierz D, Dybała T, Swiatkowska L. Expression of messenger RNA for transforming growth factor-beta1 and for transforming growth factor-beta receptors in peripheral blood of systemic lupus erythematosus patients treated with low doses of quinagolide. Autoimmunity. 2007 Feb;40(1):23-30. PubMed PMID: 17364494.

10: Barlier A, Jaquet P. Quinagolide--a valuable treatment option for hyperprolactinaemia. Eur J Endocrinol. 2006 Feb;154(2):187-95. Review. PubMed PMID: 16452531.