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MedKoo Cat#: 598723 | Name: Levodropropizine
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Description:

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

Levodropropizine is a cough suppressant. It is the levo isomer of dropropizine. It acts as a peripheral antitussive, with no action in the central nervous system.

Chemical Structure

Levodropropizine
CAS#99291-25-5

Theoretical Analysis

MedKoo Cat#: 598723

Name: Levodropropizine

CAS#: 99291-25-5

Chemical Formula: C13H20N2O2

Exact Mass: 236.1525

Molecular Weight: 236.32

Elemental Analysis: C, 66.07; H, 8.53; N, 11.85; O, 13.54

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Levodropropizine; DF 526; DF-526; DF526; Levotuss;
IUPAC/Chemical Name
(S)-3-(4-phenylpiperazin-1-yl)propane-1,2-diol
InChi Key
PTVWPYVOOKLBCG-ZDUSSCGKSA-N
InChi Code
InChI=1S/C13H20N2O2/c16-11-13(17)10-14-6-8-15(9-7-14)12-4-2-1-3-5-12/h1-5,13,16-17H,6-11H2/t13-/m0/s1
SMILES Code
OC[C@@H](O)CN1CCN(C2=CC=CC=C2)CC1
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levodropropizine (DF-526) is a histamine receptor inhibitor.
In vitro activity:
TBD
In vivo activity:
Levodropropizine (LVDP) is an effective antitussive drug. Its effects on single-unit discharge of vagal afferent C-fibres were tested in anaesthetized cats to assess whether an inhibition of vagal C-fibres is involved in its antitussive properties. LVDP reduced both the duration of apnoea and the response of the C-fibre to PBG. The LVDP-induced inhibition of the C-fibre response to PBG was on average 50% in pulmonary and 25% in non-pulmonary fibres. Reference: Br J Pharmacol. 1996 Mar;117(5):853-8. https://pubmed.ncbi.nlm.nih.gov/8851501/
Solvent mg/mL mM comments
Solubility
DMF 30.0 126.95
DMSO 42.3 179.14
Ethanol 24.0 101.56
PBS (pH 7.2) 1.0 4.23
Water 12.5 52.90
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 236.32 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. Shams H, Daffonchio L, Scheid P. Effects of levodropropizine on vagal afferent C-fibres in the cat. Br J Pharmacol. 1996 Mar;117(5):853-8. doi: 10.1111/j.1476-5381.1996.tb15271.x. PMID: 8851501; PMCID: PMC1909426. 2. Yamawaki I, Geppetti P, Bertrand C, Huber O, Daffonchio L, Omini C, Nadel JA. Levodropropizine reduces capsaicin- and substance P-induced plasma extravasation in the rat trachea. Eur J Pharmacol. 1993 Oct 12;243(1):1-6. doi: 10.1016/0014-2999(93)90159-f. PMID: 7504629.
In vitro protocol:
TBD
In vivo protocol:
1. Shams H, Daffonchio L, Scheid P. Effects of levodropropizine on vagal afferent C-fibres in the cat. Br J Pharmacol. 1996 Mar;117(5):853-8. doi: 10.1111/j.1476-5381.1996.tb15271.x. PMID: 8851501; PMCID: PMC1909426. 2. Yamawaki I, Geppetti P, Bertrand C, Huber O, Daffonchio L, Omini C, Nadel JA. Levodropropizine reduces capsaicin- and substance P-induced plasma extravasation in the rat trachea. Eur J Pharmacol. 1993 Oct 12;243(1):1-6. doi: 10.1016/0014-2999(93)90159-f. PMID: 7504629.
1: Zanasi A, Lanata L, Fontana G, Saibene F, Dicpinigaitis P, De Blasio F. Levodropropizine for treating cough in adult and children: a meta-analysis of published studies. Multidiscip Respir Med. 2015 May 31;10(1):19. doi: 10.1186/s40248-015-0014-3. eCollection 2015. PubMed PMID: 26097707; PubMed Central PMCID: PMC4472410. 2: Jang JW, Seo JH, Jo MH, Lee YJ, Cho YW, Yim SV, Lee KT. Relative bioavailability of levodropropizine 60 mg capsule and syrup formulations in healthy male Korean volunteers: a singledose, randomized-sequence, open-label, two-way crossover study. Int J Clin Pharmacol Ther. 2013 Feb;51(2):152-60. PubMed PMID: 23351597. 3: Cao QR, Piao YN, Choi JS, Liu Y, Yang M, Cui JH. Design, in vitro release characterization and pharmacokinetics of novel controlled release pellets containing levodropropizine. Pharm Dev Technol. 2014 May;19(3):296-303. doi: 10.3109/10837450.2013.778871. Epub 2013 Mar 19. PubMed PMID: 23509871. 4: Park KH, Yun IS, Choi SY, Lee JH, Hong CS, Park JW. A case of immunoglobulin E mediated anaphylaxis to levodropropizine. Yonsei Med J. 2013 Jan 1;54(1):262-4. doi: 10.3349/ymj.2013.54.1.262. PubMed PMID: 23225830; PubMed Central PMCID: PMC3521276. 5: Schildmann EK, Rémi C, Bausewein C. Levodropropizine in the management of cough associated with cancer or nonmalignant chronic disease--a systematic review. J Pain Palliat Care Pharmacother. 2011;25(3):209-18. doi: 10.3109/15360288.2011.583979. Epub 2011 Aug 1. Review. PubMed PMID: 21806417. 6: De Blasio F, Dicpinigaitis PV, De Danieli G, Lanata L, Zanasi A. Efficacy of levodropropizine in pediatric cough. Pulm Pharmacol Ther. 2012 Oct;25(5):337-42. doi: 10.1016/j.pupt.2012.05.010. Epub 2012 Jul 4. Review. PubMed PMID: 22771902. 7: Kumar PA, Raju TV, Thirupathi D, Kumar R, Shree J. Development and Validation of a Stability-Indicating LC-Method for the Simultaneous Estimation of Levodropropizine, Chloropheniramine, Methylparaben, Propylparaben, and Levodropropizine Impurities. Sci Pharm. 2013 Jan-Mar;81(1):139-50. doi: 10.3797/scipharm.1210-18. Epub 2012 Nov 17. PubMed PMID: 23641334; PubMed Central PMCID: PMC3617657. 8: Bruschi C, Crotti P, Dacosto E, Fanfulla F, Daffonchio L, Novellini R. Levodropropizine does not affect P0.1 and breathing pattern in healthy volunteers and patients with chronic respiratory impairment. Pulm Pharmacol Ther. 2003;16(4):231-6. PubMed PMID: 12850126. 9: Yamawaki I, Geppetti P, Bertrand C, Huber O, Daffonchio L, Omini C, Nadel JA. Levodropropizine reduces capsaicin- and substance P-induced plasma extravasation in the rat trachea. Eur J Pharmacol. 1993 Oct 12;243(1):1-6. PubMed PMID: 7504629. 10: Zhao LM, Zhao L, Sun YX, Qiu F, Guo SB. [Determination of levodropropizine and its pharmacokinetics in human plasma using LC/MS/MS]. Yao Xue Xue Bao. 2004 Dec;39(12):993-6. Chinese. PubMed PMID: 15813028. 11: Luporini G, Barni S, Marchi E, Daffonchio L. Efficacy and safety of levodropropizine and dihydrocodeine on nonproductive cough in primary and metastatic lung cancer. Eur Respir J. 1998 Jul;12(1):97-101. PubMed PMID: 9701421. 12: Catena E, Daffonchio L. Efficacy and tolerability of levodropropizine in adult patients with non-productive cough. Comparison with dextromethorphan. Pulm Pharmacol Ther. 1997;10(2):89-96. PubMed PMID: 9425640. 13: Daffonchio L, Hernandez A, Melillo G, Clavenna G, Omini C. Effectiveness of levodropropizine against cigarette smoke-induced airway hyperreactivity: possible mechanism. Eur J Pharmacol. 1993 Apr 1;228(5-6):257-61. PubMed PMID: 7683266. 14: Bossi R, Braga PC, Centanni S, Legnani D, Moavero NE, Allegra L. Antitussive activity and respiratory system effects of levodropropizine in man. Arzneimittelforschung. 1988 Aug;38(8):1159-62. PubMed PMID: 3196411. 15: Miceli Sopo S, Greco M, Monaco S, Varrasi G, Di Lorenzo G, Simeone G; Milk Honey Study (M&HS) Group. Effect of multiple honey doses on non-specific acute cough in children. An open randomised study and literature review. Allergol Immunopathol (Madr). 2015 Sep-Oct;43(5):449-55. doi: 10.1016/j.aller.2014.06.002. Epub 2014 Sep 6. PubMed PMID: 25201759. 16: Gatti G, Barzaghi N, Dominijanni R, Cordaro C, Perucca E. Enantioselective effects of levodropropizine and dropropizine on psychomotor functions in normal volunteers: a placebo-controlled, double-blind comparative study. Drugs Exp Clin Res. 1993;19(1):33-9. PubMed PMID: 8223138. 17: Banderali G, Riva E, Fiocchi A, Cordaro CI, Giovannini M. Efficacy and tolerability of levodropropizine and dropropizine in children with non-productive cough. J Int Med Res. 1995 May-Jun;23(3):175-83. PubMed PMID: 7649341. 18: Melillo G, Malandrino S, Rossoni G, Caselli G, Bestetti A, Borsa M, Tonon GC, Berti F. General pharmacology of the new antitussive levodropropizine. Arzneimittelforschung. 1988 Aug;38(8):1144-50. PubMed PMID: 3196408. 19: Lavezzo A, Melillo G, Clavenna G, Omini C. Peripheral site of action of levodropropizine in experimentally-induced cough: role of sensory neuropeptides. Pulm Pharmacol. 1992 Jun;5(2):143-7. PubMed PMID: 1611233. 20: Borsa M, Glavenna G, Ferrari MP, Canali S, Giachetti C, Zanolo G. Linearity of levodropropizine, a new antitussive drug, in the healthy volunteer. Eur J Drug Metab Pharmacokinet. 1991;Spec No 3:178-84. PubMed PMID: 1820875.

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BMS-986202

BMS-986202

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