Quinagolide HCl | CAS#: 94424-50-7 | CAS#87056-78-8 | prolactin-release inhibitor

MedKoo Cat#: 202390 | Name: Quinagolide HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Quinagolide HCl

CAS#94424-50-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 202390

Name: Quinagolide HCl

CAS#: 94424-50-7 (HCl)

Chemical Formula: C20H34ClN3O3S

Exact Mass: 0.0000

Molecular Weight: 432.02

Elemental Analysis: C, 55.60; H, 7.93; Cl, 8.21; N, 9.73; O, 11.11; S, 7.42

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

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)

Product Data

Product Data

Certificate of Analysis

View previous batch of CoA

QC Data

View previous batch NMR, HPLC, and MS

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	3.9	8.91

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

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: GÃ³mez R, Abad A, Delgado F, Tamarit S, SimÃ³n 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, SzÃ¼cs N, Kender Z, CzirjÃ¡k S, RÃ¡cz 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, FernÃ¡ndez-SÃ¡nchez M, GarcÃa-Velasco JA, Landeras J, Ballesteros A, MuÃ±oz E, GonzÃ¡lez S, SimÃ³n 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. 11: Roy KS, Prakash BS. Plasma progesterone, oestradiol-17β and total oestrogen profiles in relation to oestrous behaviour during induced ovulation in Murrah buffalo heifers. J Anim Physiol Anim Nutr (Berl). 2009 Aug;93(4):486-95. doi: 10.1111/j.1439-0396.2008.00830.x. PMID: 18507697. 12: Mostafa AA, Bebawy LI, Refaat HH. Spectrophotometric determination of clobetasol propionate, halobetasol propionate, quinagolide hydrochloride, through charge transfer complexation. J Pharm Biomed Anal. 2002 Mar 1;27(6):889-99. doi: 10.1016/s0731-7085(01)00581-7. PMID: 11836053.