Synonym
BW 443C; BW-443C; BW443C; Tyr-arg-gly-(4-nitro-phe)-pro-NH2;
IUPAC/Chemical Name
(S)-1-((S)-2-(2-((R)-2-((S)-2-amino-3-(4-hydroxyphenyl)propanamido)-5-guanidinopentanamido)acetamido)-3-(4-nitrophenyl)propanoyl)pyrrolidine-2-carboxamide diacetate
InChi Key
IDHPVZFSVGWIIP-WMEHTASQSA-N
InChi Code
InChI=1S/C31H42N10O8.2C2H4O2/c32-22(15-18-7-11-21(42)12-8-18)28(45)39-23(3-1-13-36-31(34)35)29(46)37-17-26(43)38-24(16-19-5-9-20(10-6-19)41(48)49)30(47)40-14-2-4-25(40)27(33)44;2*1-2(3)4/h5-12,22-25,42H,1-4,13-17,32H2,(H2,33,44)(H,37,46)(H,38,43)(H,39,45)(H4,34,35,36);2*1H3,(H,3,4)/t22-,23+,24-,25-;;/m0../s1
SMILES Code
O=C(N)[C@H]1N(C([C@H](CC2=CC=C([N+]([O-])=O)C=C2)NC(CNC([C@@H](CCCNC(N)=N)NC([C@H](CC3=CC=C(O)C=C3)N)=O)=O)=O)=O)CCC1.CC(O)=O.CC(O)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
802.84
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 |
1: Belvisi MG, Stretton CD, Verleden GM, Ledingham SJ, Yacoub MH, Barnes PJ. Inhibition of cholinergic neurotransmission in human airways by opioids. J Appl Physiol (1985). 1992 Mar;72(3):1096-100. PubMed PMID: 1314798.
2: Adcock JJ. Peripheral opioid receptors and the cough reflex. Respir Med. 1991 Jan;85 Suppl A:43-6. Review. PubMed PMID: 1852031.
3: Yeadon M, Wilkinson D, Darley-Usmar V, O'Leary VJ, Payne AN. Mechanisms contributing to ozone-induced bronchial hyperreactivity in guinea-pigs. Pulm Pharmacol. 1992;5(1):39-50. PubMed PMID: 1375522.
4: Calatayud S, Quintana E, Esplugues J, Barrachina MD. Role of central oxytocin in the inhibition by endotoxin of distension-stimulated gastric acid secretion. Naunyn Schmiedebergs Arch Pharmacol. 1999 Dec;360(6):676-82. PubMed PMID: 10619185.
5: Bolser DC, DeGennaro FC, O'Reilly S, Chapman RW, Kreutner W, Egan RW, Hey JA. Peripheral and central sites of action of GABA-B agonists to inhibit the cough reflex in the cat and guinea pig. Br J Pharmacol. 1994 Dec;113(4):1344-8. PubMed PMID: 7889290; PubMed Central PMCID: PMC1510532.
6: Adcock JJ, Schneider C, Smith TW. Effects of codeine, morphine and a novel opioid pentapeptide BW443C, on cough, nociception and ventilation in the unanaesthetized guinea-pig. Br J Pharmacol. 1988 Jan;93(1):93-100. PubMed PMID: 3349236; PubMed Central PMCID: PMC1853787.
7: Posner J, Dean K, Jeal S, Moody SG, Peck AW, Rutter G, Telekes A. A preliminary study of the pharmacodynamics and pharmacokinetics of a novel enkephalin analogue [Tyr-D.Arg-Gly-Phe (4NO2).Pro.NH2 (BW443C)] in healthy volunteers. Eur J Clin Pharmacol. 1988;34(1):67-71. PubMed PMID: 3360050.
8: Esplugues JV, Barrachina MD, Esplugues J. Modulation by peripheral opioids of basal and distension-stimulated gastric acid secretion in the rat. Br J Pharmacol. 1992 May;106(1):33-8. PubMed PMID: 1504729; PubMed Central PMCID: PMC1907452.
9: Follenfant RL, Hardy GW, Lowe LA, Schneider C, Smith TW. Antinociceptive effects of the novel opioid peptide BW443C compared with classical opiates; peripheral versus central actions. Br J Pharmacol. 1988 Jan;93(1):85-92. PubMed PMID: 3349235; PubMed Central PMCID: PMC1853761.
10: Shankley CE, Anderson CW, Adcock JJ. Effect of BW443C81, a novel opioid, on non-cholinergic bronchoconstrictor responses and neurogenic plasma extravasation in the guinea pig. Agents Actions. 1992 May;36(1-2):22-8. PubMed PMID: 1414685.
11: Buchan P, Adcock JJ. Capsaicin-induced bronchoconstriction in the guinea-pig: contribution of vagal cholinergic reflexes, local axon reflexes and their modulation by BW443C81. Br J Pharmacol. 1992 Feb;105(2):448-52. PubMed PMID: 1559133; PubMed Central PMCID: PMC1908653.
