Dihydrocodeine bitartrateProduct ingredient for Dihydrocodeine

Name
Dihydrocodeine bitartrate
Drug Entry
Dihydrocodeine

Dihydrocodeine is an opioid analgesic used as an alternative or adjunct to codeine to treat moderate to severe pain, severe dyspnea, and cough.

It is semi-synthetic, and was developed in Germany in 1908 during an international search to find a more effective antitussive agent to help reduce the spread of airborne infectious diseases such as tuburculosis. It was marketed in 1911.

Accession Number
DBSALT000048  (DBSALT000055)
Structure
Synonyms
Dihydrocodeine tartrate
UNII
8LXS95BSA9
CAS Number
5965-13-9
Weight
Average: 451.467
Monoisotopic: 451.184231531
Chemical Formula
C22H29NO9
InChI Key
ZGSZBVAEVPSPFM-HYTSPMEMSA-N
InChI
InChI=1S/C18H23NO3.C4H6O6/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;5-1(3(7)8)2(6)4(9)10/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-,12+,13-,17-,18-;1-,2-/m01/s1
IUPAC Name
(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18)-trien-14-ol; (2R,3R)-2,3-dihydroxybutanedioic acid
SMILES
[H][C@](O)(C(O)=O)[C@@]([H])(O)C(O)=O.[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3OC
PubChem Compound
5492624
ChemSpider
4591081
Wikipedia
Dihydrocodeine
Predicted Properties
PropertyValueSource
Water Solubility2.38 mg/mLALOGPS
logP1.58ALOGPS
logP1.55Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)14.15Chemaxon
pKa (Strongest Basic)9.33Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.93 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity83.64 m3·mol-1Chemaxon
Polarizability32.82 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon