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MedKoo Cat#: 555688 | Name: ORG-43553

Description:

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

ORG-43553 is the first low-molecular-weight agonistic and allosteric radioligand for the human luteinizing hormone receptor.

Chemical Structure

ORG-43553
ORG-43553
CAS#501444-88-8 (free base)

Theoretical Analysis

MedKoo Cat#: 555688

Name: ORG-43553

CAS#: 501444-88-8 (free base)

Chemical Formula: C24H30N6O3S2

Exact Mass: 514.1821

Molecular Weight: 514.66

Elemental Analysis: C, 56.01; H, 5.88; N, 16.33; O, 9.33; S, 12.46

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.
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Related CAS #
501444-89-9 (TFA) 501444-88-8 (free base)
Synonym
ORG-43553; ORG 43553; ORG43553;
IUPAC/Chemical Name
5-Amino-N-(1,1-dimethylethyl)-2-(methylthio)-4-[3-[[2-(4-morpholinyl)acetyl]amino]phenyl]thieno[2,3-d]pyrimidine-6-carboxamide
InChi Key
UWTXKCMCTINMHD-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H30N6O3S2/c1-24(2,3)29-21(32)20-18(25)17-19(27-23(34-4)28-22(17)35-20)14-6-5-7-15(12-14)26-16(31)13-30-8-10-33-11-9-30/h5-7,12H,8-11,13,25H2,1-4H3,(H,26,31)(H,29,32)
SMILES Code
O=C(C1=C(N)C2=C(C3=CC=CC(NC(CN4CCOCC4)=O)=C3)N=C(SC)N=C2S1)NC(C)(C)C
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
Shelf Life
>3 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
The luteinizing hormone (LH) receptor plays a pivotal role in reproduction. The high-molecular-weight (HMW) human chorionic gonadotropin (hCG) and LH are the endogenous ligands of this receptor and bind to its large N terminus.

Preparing Stock Solutions

The following data is based on the product molecular weight 514.66 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
1: Newton CL, Anderson RC. Pharmacoperones for Misfolded Gonadotropin Receptors. Handb Exp Pharmacol. 2018;245:111-134. doi: 10.1007/164_2017_64. Review. PubMed PMID: 29043503. 2: Derkach KV, Legkodukh AS, Dar’in DV, Shpakov AO. THE STIMULATING EFFECT OF THIENOPYRIMIDINES, THE STRUCTURAL ANALOGS OF ORG 43553, ON THE ACTIVITY OF ADENYLYL CYCLASE IN THE TESTES AND ON THE TESTOSTERONE PRODUCTION IN MALE RATS. Tsitologiia. 2016;58(8):602-9. English, Russian. PubMed PMID: 30183200. 3: Shpakov AO, Derkach KV, Dar'in DV, Lobanov PS. [Activation of adenylyl cyclase in rats testes and ovaries using thienopyrimidine derivatives]. Tsitologiia. 2014;56(5):346-52. Russian. PubMed PMID: 25696974. 4: Gerrits M, Mannaerts B, Kramer H, Addo S, Hanssen R. First evidence of ovulation induced by oral LH agonists in healthy female volunteers of reproductive age. J Clin Endocrinol Metab. 2013 Apr;98(4):1558-66. doi: 10.1210/jc.2012-3404. Epub 2013 Mar 20. PubMed PMID: 23515453. 5: Heitman LH, Kleinau G, Brussee J, Krause G, Ijzerman AP. Determination of different putative allosteric binding pockets at the lutropin receptor by using diverse drug-like low molecular weight ligands. Mol Cell Endocrinol. 2012 Apr 4;351(2):326-36. doi: 10.1016/j.mce.2012.01.010. Epub 2012 Jan 18. PubMed PMID: 22269095. 6: Goebel C. Stimulating luteinizing hormone. Drug Test Anal. 2011 Nov-Dec;3(11-12):868-72. doi: 10.1002/dta.393. Epub 2011 Dec 6. PubMed PMID: 22147514. 7: Heitman LH, Narlawar R, de Vries H, Willemsen MN, Wolfram D, Brussee J, Ijzerman AP. Substituted terphenyl compounds as the first class of low molecular weight allosteric inhibitors of the luteinizing hormone receptor. J Med Chem. 2009 Apr 9;52(7):2036-42. doi: 10.1021/jm801561h. Erratum in: J Med Chem. 2010 Jan 14;53(1):520. PubMed PMID: 19296599. 8: van de Lagemaat R, Timmers CM, Kelder J, van Koppen C, Mosselman S, Hanssen RG. Induction of ovulation by a potent, orally active, low molecular weight agonist (Org 43553) of the luteinizing hormone receptor. Hum Reprod. 2009 Mar;24(3):640-8. doi: 10.1093/humrep/den412. Epub 2008 Dec 16. PubMed PMID: 19088107. 9: van Koppen CJ, Zaman GJ, Timmers CM, Kelder J, Mosselman S, van de Lagemaat R, Smit MJ, Hanssen RG. A signaling-selective, nanomolar potent allosteric low molecular weight agonist for the human luteinizing hormone receptor. Naunyn Schmiedebergs Arch Pharmacol. 2008 Nov;378(5):503-14. doi: 10.1007/s00210-008-0318-3. Epub 2008 Jun 13. PubMed PMID: 18551279. 10: Heitman LH, Oosterom J, Bonger KM, Timmers CM, Wiegerinck PH, Ijzerman AP. [3H]Org 43553, the first low-molecular-weight agonistic and allosteric radioligand for the human luteinizing hormone receptor. Mol Pharmacol. 2008 Feb;73(2):518-24. Epub 2007 Nov 7. PubMed PMID: 17989351.

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