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MedKoo Cat#: 574966 | Name: Aprofene hydrochloride

Description:

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

Aprofene, also known as aprophen, is an antagonist of muscarinic and nicotinic acetylcholine receptors. It may be used in the treatment of endarteritis (inflammation of the inner shell of the artery), peptic ulcers, spastic colitis (inflammation of the colon characterized by sharp contractions), cholecystitis (inflammation of the gallbladder).

Chemical Structure

Aprofene hydrochloride
CAS#2589-00-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 574966

Name: Aprofene hydrochloride

CAS#: 2589-00-6 (HCl)

Chemical Formula: C21H28ClNO2

Exact Mass: 361.1809

Molecular Weight: 361.91

Elemental Analysis: C, 69.69; H, 7.80; Cl, 9.80; N, 3.87; O, 8.84

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 #
2589-00-6 (HCl) 3563-01-7 (free base)
Synonym
Aprophen hydrochloride; Aprofen hydrochloride; Aprofene hydrochloride; Aprofene HCl
IUPAC/Chemical Name
Propionic acid, 2,2-diphenyl-, 2-(diethylamino)ethyl ester, hydrochloride
InChi Key
UKPBAERJQQMCIP-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H27NO2.ClH/c1-4-22(5-2)16-17-24-20(23)21(3,18-12-8-6-9-13-18)19-14-10-7-11-15-19;/h6-15H,4-5,16-17H2,1-3H3;1H
SMILES Code
Cl.CCN(CC)CCOC(=O)C(C)(c1ccccc1)c2ccccc2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 361.91 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: Arima N, Uchida Y, Yu R, Nakayama K, Nishina H. Acetylcholine receptors regulate gene expression that is essential for primitive streak formation in murine embryoid bodies. Biochem Biophys Res Commun. 2013 Jun 7;435(3):447-53. doi: 10.1016/j.bbrc.2013.05.006. Epub 2013 May 10. PMID: 23665324. 2: Leader H, Wolfe AD, Chiang PK, Gordon RK. Pyridophens: binary pyridostigmine- aprophen prodrugs with differential inhibition of acetylcholinesterase, butyrylcholinesterase, and muscarinic receptors. J Med Chem. 2002 Feb 14;45(4):902-10. doi: 10.1021/jm010196t. PMID: 11831902. 3: Leader H, Gordon RK, Baumgold J, Boyd VL, Newman AH, Smejkal RM, Chiang PK. Muscarinic receptor subtype specificity of (N,N-dialkylamino)alkyl 2-cyclohexyl-2-phenylpropionates: cylexphenes (cyclohexyl-substituted aprophen analogues). J Med Chem. 1992 Apr 3;35(7):1290-5. doi: 10.1021/jm00085a017. PMID: 1560441. 4: Brown ND, Phillips LR, Leader H, Chiang PK. Isolation and identification of beta-hydroxyethylaprophen: a urinary metabolite of aprophen in rats. J Chromatogr. 1991 Feb 15;563(2):466-71. doi: 10.1016/0378-4347(91)80057-j. PMID: 2056011. 5: Newman AH, Covington J, Oleshansky M, Jackson BW, Weissman BA, Leader H, Chiang PK. Aprophit: an irreversible antagonist for muscarinic receptors. Biochem Pharmacol. 1990 Sep 15;40(6):1357-64. doi: 10.1016/0006-2952(90)90404-9. PMID: 2403389. 6: Genovese RF, Elsmore TF, Witkin JM. Relationship of the behavioral effects of aprophen, atropine and scopolamine to antagonism of the behavioral effects of physostigmine. Pharmacol Biochem Behav. 1990 Sep;37(1):117-22. doi: 10.1016/0091-3057(90)90051-i. PMID: 2263653. 7: Karle JM, Karle IL, Chiang PK. Structural comparison of the potent antimuscarinic agent azaprophen hydrochloride with aprophen hydrochloride and structurally related antimuscarinic agents. Acta Crystallogr B. 1990 Apr 1;46 ( Pt 2):215-22. doi: 10.1107/s0108768189010967. PMID: 2344395. 8: Grudev D. Razhdane pri prenosena bremennost sled podgotovka i induktsiia s aprofen i prednizolon [Delivery in prolonged pregnancy following preparation and induction with aprofen and prednisolone]. Akush Ginekol (Sofiia). 1990;29(3):14-8. Bulgarian. PMID: 2252139. 9: Leader H, Smejkal RM, Payne CS, Padilla FN, Doctor BP, Gordon RK, Chiang PK. Binary antidotes for organophosphate poisoning: aprophen analogues that are both antimuscarinics and carbamates. J Med Chem. 1989 Jul;32(7):1522-8. doi: 10.1021/jm00127a020. PMID: 2738887. 10: Wolthuis OL, Philippens IH, Vanwersch RA. Side effects of therapeutic drugs against organophosphate poisoning. Neurotoxicol Teratol. 1989 May- Jun;11(3):221-5. doi: 10.1016/0892-0362(89)90062-7. PMID: 2666846. 11: Beach JE, Smallridge RC, Chiang PK, Fein HG. Reversal of inhibition of prolactin secretion in cultured pituitary cells by muscarinic antagonists. J Pharmacol Exp Ther. 1988 Aug;246(2):548-52. PMID: 3404446. 12: Nakazato Y, Oleshansky MA, Chiang PK. Effects of muscarinic pharmacophores on the cholinergic regulation of catecholamine secretion from perfused adrenal glands. Arch Int Pharmacodyn Ther. 1988 May-Jun;293:209-18. PMID: 3421778. 13: Brown ND, Smejkal RM, Breuer E, Doctor BP, Chiang PK. Desethylaprophen: a metabolite of aprophen with antimuscarinic activities. J Pharm Sci. 1988 Feb;77(2):145-8. doi: 10.1002/jps.2600770210. PMID: 3258910. 14: Pohorecki R, Head R, Domino EF. Effects of selected muscarinic cholinergic antagonists on [3H]acetylcholine release from rat hippocampal slices. J Pharmacol Exp Ther. 1988 Jan;244(1):213-7. PMID: 3335998. 15: Khadzhiev A, Dimitrova V, Filipov E. Rezultati ot induktsiiata na razhdaneto s aprofen [The results of inducing labor with aprofen]. Akush Ginekol (Sofiia). 1988;27(6):38-41. Bulgarian. PMID: 3245549. 16: Grudev D, Novachkov L, Geshev G, Krushkov I. Prilozhenie na aprophen za podgotovka i induktsiia na razhdaneto [Use of aprophen in the preparation for and induction of labor]. Akush Ginekol (Sofiia). 1988;27(4):39-43. Bulgarian. PMID: 3218679. 17: Amitai G, Herz JM, Bruckstein R, Luz-Chapman S. The muscarinic antagonists aprophen and benactyzine are noncompetitive inhibitors of the nicotinic acetylcholine receptor. Mol Pharmacol. 1987 Nov;32(5):678-85. PMID: 3683366. 18: Rush RS, Doctor BP, Wolfe AD. Kinetic investigations into the interactions of aprophen with cholinesterases and a carboxylesterase. Biochem Pharmacol. 1986 Dec 1;35(23):4167-70. doi: 10.1016/0006-2952(86)90691-x. PMID: 3098245. 19: Aarbakke J, Miura GA, Brown ND, Gray RR, Gordon RK, Doctor BP, Chiang PK. Disposition of aprophen in rats. J Pharm Pharmacol. 1986 Dec;38(12):928-30. doi: 10.1111/j.2042-7158.1986.tb03387.x. PMID: 2880971. 20: Leadbeater L, Inns RH, Rylands JM. Treatment of poisoning by soman. Fundam Appl Toxicol. 1985 Dec;5(6 Pt 2):S225-31. doi: 10.1016/0272-0590(85)90132-0. PMID: 4092890.