diamorphine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
opioid receptor antagonists/agonists, morphinan derivates 4412 561-27-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • diamorphine hydrochloride
  • diacetylmorphine hydrochloride
  • heroin
  • diamorphine
  • acetomorphin
  • acetomorphine
  • diacetylmorphine
  • diamorphine HCl
  • diacetylmorphine HCl
A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed)
  • Molecular weight: 369.42
  • Formula: C21H23NO5
  • CLOGP: 1.57
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 0
  • TPSA: 65.07
  • ALOGS: -3.14
  • ROTB: 4
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BA (Bioavailability) 30 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.31 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 212.30 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.06 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.435 Moderate 0.66
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.324 Moderate 0.66
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 22.594 10^-6 cm/s Moderate 0.66
dh-clint Dog hepatocyte intrinsic clearance 82.985 uL/min/10^6 cells Moderate 0.66
dppb Dog plasma protein binding (% unbound) 63.420 % Moderate 0.66
fcs-ppb Fetal calf serum protein binding (% unbound) 57.150 % Moderate 0.66
herg hERG pIC50 4.820 pIC50 Moderate 0.66
hh-clint Human hepatocyte intrinsic clearance 71.614 uL/min/10^6 cells Moderate 0.66
hlm-clint Human liver microsomal intrinsic clearance 230.144 uL/min/mg protein Moderate 0.66
hppb Human plasma protein binding (% unbound) 58.330 % Moderate 0.66
kinase-safety-class ACVR2A,ACVR2B,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK2,CDK4,CDK5,CDK9,CHEK1,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,IGF1R,ITK,JAK2,JAK3,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MET,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ZAP70 59
kinase-selectivity-class AXL,BRAF,EIF2AK3,GRK2,MAP2K6,STK33,TEK 7
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 2.518 Moderate 0.66
mh-clint Mouse hepatocyte intrinsic clearance 267.301 Moderate 0.66
mppb Mouse plasma protein binding (% unbound) 57.430 Moderate 0.66
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 6.887 Moderate 0.66
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 77.370 % Moderate 0.66
rh-clint Rat hepatocyte intrinsic clearance 245.471 uL/min/10^6 cells Moderate 0.66
rh-fuinc Rat hepatocyte fraction unbound in incubation 84.360 % Moderate 0.66
rppb Rat plasma protein binding (% unbound) 55.160 % Moderate 0.66
solubility-dd Solubility at pH 7.4 in DMSO 939.723 uM Moderate 0.66

Approvals:

None

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 4307.57 83.58 953 3749 81394 90542351
Toxicity to various agents 1167.58 83.58 464 4238 287382 90336363
Cardio-respiratory arrest 654.82 83.58 206 4496 62934 90560811
Respiratory arrest 483.45 83.58 141 4561 33170 90590575
Cardiac arrest 375.31 83.58 156 4546 104779 90518966
Completed suicide 332.95 83.58 158 4544 144900 90478845
Drug dependence 219.43 83.58 75 4627 29252 90594493
Overdose 206.39 83.58 118 4584 157591 90466154
Death 201.14 83.58 175 4527 456376 90167369
Intentional product misuse 164.44 83.58 84 4618 89520 90534225
Asphyxia 148.02 83.58 40 4662 7063 90616682
Drug use disorder 146.20 83.58 41 4661 8302 90615443
Substance abuse 124.73 83.58 33 4669 5373 90618372
Myocardial stunning 122.38 83.58 20 4682 293 90623452
Substance use disorder 117.54 83.58 26 4676 1994 90621751
Poisoning 98.62 83.58 35 4667 15182 90608563
Respiratory depression 94.07 83.58 34 4668 15541 90608204

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 8987.05 58.90 2481 8793 102290 42507771
Toxicity to various agents 2463.18 58.90 1187 10087 227949 42382112
Drug dependence 704.95 58.90 271 11003 28823 42581238
Respiratory arrest 528.92 58.90 219 11055 28205 42581856
Cardio-respiratory arrest 488.33 58.90 259 11015 58377 42551684
Overdose 483.17 58.90 316 10958 104948 42505113
Intentional product misuse 458.52 58.90 253 11021 61647 42548414
Asphyxia 326.85 58.90 111 11163 8215 42601846
Substance abuse 288.94 58.90 103 11171 8802 42601259
Cardiac arrest 240.75 58.90 212 11062 109108 42500953
Poisoning 229.02 58.90 100 11174 14599 42595462
Respiratory depression 226.43 58.90 107 11167 18761 42591300
Pulmonary oedema 207.88 58.90 145 11129 53127 42556934
Substance use disorder 196.99 58.90 68 11206 5277 42604784
Depressed level of consciousness 192.83 58.90 133 11141 47837 42562224
Death 178.07 58.90 386 10888 470799 42139262
Drug use disorder 176.37 58.90 75 11199 10258 42599803
Bradypnoea 170.10 58.90 58 11216 4335 42605726
Incorrect route of product administration 156.90 58.90 91 11183 24214 42585847
Alcohol abuse 151.08 58.90 52 11222 3997 42606064
Miosis 148.33 58.90 72 11202 13374 42596687
Coma 138.34 58.90 114 11160 53440 42556621
Drug withdrawal syndrome 129.38 58.90 77 11197 21472 42588589
Withdrawal syndrome 99.79 58.90 57 11217 14718 42595343
Drug ineffective 95.16 58.90 25 11249 630172 41979889
Diarrhoea 82.62 58.90 12 11262 460837 42149224
Off label use 81.18 58.90 34 11240 638301 41971760
Drug withdrawal syndrome neonatal 74.83 58.90 32 11242 4429 42605632
Drug abuser 71.60 58.90 29 11245 3502 42606559
Fatigue 68.08 58.90 16 11258 435625 42174436
Pyrexia 64.54 58.90 13 11261 394029 42216032
Accidental overdose 64.23 58.90 56 11218 28274 42581787
Drug diversion 62.74 58.90 19 11255 968 42609093

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 13448.66 58.82 3307 11447 174104 110400441
Toxicity to various agents 3698.09 58.82 1601 13153 478954 110095591
Cardio-respiratory arrest 1102.67 58.82 454 14300 115382 110459163
Respiratory arrest 994.11 58.82 350 14404 57949 110516596
Drug dependence 753.03 58.82 274 14480 49746 110524799
Intentional product misuse 652.97 58.82 329 14425 132575 110441970
Cardiac arrest 599.54 58.82 355 14399 196398 110378147
Overdose 535.78 58.82 352 14402 233442 110341103
Asphyxia 439.04 58.82 134 14620 14081 110560464
Death 418.32 58.82 488 14266 698381 109876164
Poisoning 341.44 58.82 133 14621 28972 110545573
Substance use disorder 332.38 58.82 93 14661 7197 110567348
Respiratory depression 315.48 58.82 129 14625 31872 110542673
Completed suicide 303.54 58.82 254 14500 242127 110332418
Drug use disorder 297.80 58.82 106 14648 17968 110556577
Pulmonary oedema 293.77 58.82 177 14577 100482 110474063
Substance abuse 255.25 58.82 86 14668 12377 110562168
Incorrect route of product administration 238.39 58.82 132 14622 63929 110510616
Miosis 235.14 58.82 94 14660 21889 110552656
Depressed level of consciousness 227.55 58.82 157 14597 112121 110462424
Bradypnoea 226.94 58.82 72 14682 8577 110565968
Coma 209.19 58.82 152 14602 117717 110456828
Alcohol abuse 207.08 58.82 59 14695 4870 110569675
Drug withdrawal syndrome 206.42 58.82 101 14653 37953 110536592
Withdrawal syndrome 160.40 58.82 80 14674 31300 110543245
Fatigue 119.75 58.82 12 14742 1215946 109358599
Drug ineffective 116.54 58.82 30 14724 1520510 109054035
Substance use 109.78 58.82 31 14723 2475 110572070
Accidental overdose 108.47 58.82 74 14680 51760 110522785
Diarrhoea 105.29 58.82 14 14740 1139491 109435054
Drug abuser 101.62 58.82 35 14719 5374 110569171
Myocardial stunning 101.49 58.82 20 14734 326 110574219
Arthralgia 90.72 58.82 3 14751 779629 109794916
Pain 80.74 58.82 15 14739 954940 109619605
Headache 78.70 58.82 12 14742 882365 109692180
Unresponsive to stimuli 77.82 58.82 66 14688 63724 110510821
Nausea 77.77 58.82 34 14720 1235656 109338889
Off label use 76.13 58.82 54 14700 1500131 109074414
Poisoning deliberate 73.33 58.82 45 14709 26286 110548259
Pyrexia 71.99 58.82 16 14738 898249 109676296
Asthenia 64.63 58.82 8 14746 688991 109885554
Dizziness 63.36 58.82 9 14745 698184 109876361
Pulmonary congestion 59.58 58.82 42 14712 30924 110543621
Condition aggravated 59.02 58.82 13 14741 734823 109839722

FDA Adverse Event Reporting System (Pediatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Sudden infant death syndrome 24.17 20.07 4 3 78 113868

Pharmacologic Action:

SourceCodeDescription
ATC N07BC06 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
DRUGS USED IN ADDICTIVE DISORDERS
Drugs used in opioid dependence
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009294 Narcotics
MeSH PA D018689 Sensory System Agents
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
CHEBI has role CHEBI:35482 opioid analgesic
CHEBI has role CHEBI:35620 vasodilator agent
CHEBI has role CHEBI:35703 xenobiotic
CHEBI has role CHEBI:38867 anaesthetic
CHEBI has role CHEBI:55322 μ-opioid receptor agonist
CHEBI has role CHEBI:76924 plant metabolite
CHEBI has role CHEBI:78298 environmental contaminant
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:176497 geroprotector
CHEBI has role CHEBI:50266 prodrug

Related Drugs by ATC class:

N07BC Drugs used in opioid dependence 5 drugs
buprenorphinelevomethadonelevomethadyl acetatelofexidinemethadone

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Severe pain indication 76948002




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.18 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
D(2) dopamine receptor GPCR Ki 7.96 CHEMBL
D(1A) dopamine receptor GPCR Ki 6.62 CHEMBL
D(3) dopamine receptor GPCR Ki 7.44 CHEMBL

External reference:

IDSource
D07286 KEGG_DRUG
4017530 VANDF
C0011892 UMLSCUI
CHEBI:27808 CHEBI
MOI PDB_CHEM_ID
CHEMBL2106627 ChEMBL_ID
CHEMBL459324 ChEMBL_ID
DB01452 DRUGBANK_ID
9082 IUPHAR_LIGAND_ID
70D95007SX UNII
5462328 PUBCHEM_CID
3304 RXNORM
d00308 MMSL
d03877 MMSL
001545 NDDF
003843 NDDF
003844 NDDF
373529000 SNOMEDCT_US
387341002 SNOMEDCT_US
396019002 SNOMEDCT_US
60881009 SNOMEDCT_US
73572009 SNOMEDCT_US
D003932 MESH_DESCRIPTOR_UI
C0026549 UMLSCUI
DB00295 DRUGBANK_ID
5288826 PUBCHEM_CID
D009020 MESH_DESCRIPTOR_UI
CHEBI:17303 CHEBI
70D95007SX INXIGHT DRUGS

Pharmaceutical products:

None