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

Stem definitionDrug idCAS RN
ergot alkaloid derivatives 1621 50-37-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • lysergide
  • D-Lysergic acid diethylamide
  • delysid
  • dextrolysergic acid diethylamide
  • LSD
  • lysergic acid diethylamide
  • d-LSD
Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.
  • Molecular weight: 323.44
  • Formula: C20H25N3O
  • CLOGP: 2.69
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 39.34
  • ALOGS: -3.08
  • ROTB: 3

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.03 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 71 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AKT2,AKT3,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK2,JAK3,KDR,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPKAPK2,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 49
kinase-selectivity-class ACVR2B,AXL,BRAF,EIF2AK3,MAP2K6,STK33 6
pfas-class PFAS structural alert (1 = True, 0 = False) 0

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1957 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

None

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 222.03 85.50 75 555 104696 42516009
Alcohol abuse 114.37 85.50 23 607 4026 42616679
Drug dependence 111.52 85.50 33 597 29061 42591644
Substance abuse 101.53 85.50 24 606 8881 42611824
Intentional product misuse 94.40 85.50 35 595 61865 42558840

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 284.41 89.54 86 689 177325 110411199
Drug dependence 180.06 89.54 46 729 49974 110538550
Substance abuse 139.99 89.54 29 746 12434 110576090
Alcohol abuse 133.46 89.54 24 751 4905 110583619
Intentional product misuse 131.71 89.54 45 730 132859 110455665

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
MeSH PA D006213 Hallucinogens
MeSH PA D011619 Psychotropic Drugs
MeSH PA D012702 Serotonin Antagonists
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
CHEBI has role CHEBI:35469 antidepressant
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35499 hallucinogen
CHEBI has role CHEBI:35941 serotonergic agonist
CHEBI has role CHEBI:51065 dopamine agonist

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

None




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.56 acidic
pKa2 6.52 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
Beta-1 adrenergic receptor GPCR Ki 6.85 CHEMBL
Beta-2 adrenergic receptor GPCR Ki 6.13 CHEMBL
D(2) dopamine receptor GPCR EC50 6.98 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 8.86 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 9.12 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 7.52 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 8.30 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 8.40 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Kd 8.52 CHEMBL
D(3) dopamine receptor GPCR Ki 6.90 WOMBAT-PK
D(1B) dopamine receptor GPCR Ki 6.47 CHEMBL
Histamine H1 receptor GPCR Ki 5.81 CHEMBL
5-hydroxytryptamine receptor 1D GPCR Ki 8.41 CHEMBL
D(4) dopamine receptor GPCR Ki 7.25 CHEMBL
5-hydroxytryptamine receptor 5A GPCR Ki 8.05 CHEMBL
5-hydroxytryptamine receptor 1E GPCR Ki 7.03 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 8.30 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.46 CHEMBL
5-hydroxytryptamine receptor 7 GPCR Ki 8.70 CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 8.42 CHEMBL
D(1A) dopamine receptor GPCR Ki 6.74 CHEMBL
5-hydroxytryptamine receptor 6 GPCR AGONIST Ki 8.70 IUPHAR
Serotonin 2 (5-HT2) receptor GPCR Ki 8.60 CHEMBL

External reference:

IDSource
C0024334 UMLSCUI
CHEBI:6605 CHEBI
7LD PDB_CHEM_ID
CHEMBL263881 ChEMBL_ID
DB04829 DRUGBANK_ID
5761 PUBCHEM_CID
17 IUPHAR_LIGAND_ID
729 INN_ID
8NA5SWF92O UNII
001637 NDDF
15698006 SNOMEDCT_US
D008238 MESH_DESCRIPTOR_UI
8NA5SWF92O INXIGHT DRUGS

Pharmaceutical products:

None