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dihydroergotamine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| ergot alkaloid derivatives | 888 | 511-12-6 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 1 | mg | N |
| 4 | mg | O |
| 4 | mg | P |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| MRTD (Maximum Recommended Therapeutic Daily Dose) | 0.07 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 2 | Bocci G, Oprea TI, Benet LZ |
| BA (Bioavailability) | 1 % | Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H |
| Vd (Volume of distribution) | 0.33 L/kg | Lombardo F, Berellini G, Obach RS |
| CL (Clearance) | 15.07 mL/min/kg | Lombardo F, Berellini G, Obach RS |
| fu (Fraction unbound in plasma) | 0.07 % | Lombardo F, Berellini G, Obach RS |
| t_half (Half-life) | 0.55 hours | Lombardo F, Berellini G, Obach RS |
| S (Water solubility) | 0.07 mg/mL | Bocci G, Oprea TI, Benet LZ |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | 2.398 | High | 0.86 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 23.768 | High | 0.86 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 2.985 | 10^-6 cm/s | High | 0.86 |
| dh-clint | Dog hepatocyte intrinsic clearance | 3.491 | uL/min/10^6 cells | High | 0.86 |
| dppb | Dog plasma protein binding (% unbound) | 15.220 | % | High | 0.86 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 29.950 | % | High | 0.86 |
| herg | hERG pIC50 | 4.638 | pIC50 | High | 0.86 |
| hh-clint | Human hepatocyte intrinsic clearance | 2.871 | uL/min/10^6 cells | High | 0.86 |
| hlm-clint | Human liver microsomal intrinsic clearance | 33.574 | uL/min/mg protein | High | 0.86 |
| hppb | Human plasma protein binding (% unbound) | 21.790 | % | High | 0.86 |
| kinase-safety-class | ACVR2B,AXL,BRAF,BTK,CAMK2D,CDK5,EIF2AK3,ERBB2,GRK2,ITK,MAPK10,PDK1,PDK2,PDK4,PRKDC | 15 | |||
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 12.388 | High | 0.86 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 28.973 | High | 0.86 | |
| mppb | Mouse plasma protein binding (% unbound) | 13.170 | High | 0.86 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 38.194 | High | 0.86 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 25.750 | % | High | 0.86 |
| rh-clint | Rat hepatocyte intrinsic clearance | 26.546 | uL/min/10^6 cells | High | 0.86 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 65.220 | % | High | 0.86 |
| rppb | Rat plasma protein binding (% unbound) | 12.300 | % | High | 0.86 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 788.860 | uM | High | 0.86 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| April 12, 1946 | FDA | VALEANT |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Neovascularisation | 311.89 | 38.56 | 50 | 1975 | 1580 | 90624842 |
| Paradoxical drug reaction | 248.81 | 38.56 | 50 | 1975 | 5716 | 90620706 |
| Extrapyramidal disorder | 207.01 | 38.56 | 52 | 1973 | 16251 | 90610171 |
| Anuria | 201.81 | 38.56 | 50 | 1975 | 14768 | 90611654 |
| Drug ineffective for unapproved indication | 124.24 | 38.56 | 49 | 1976 | 66595 | 90559827 |
| Treatment failure | 120.47 | 38.56 | 78 | 1947 | 303850 | 90322572 |
| Reversible cerebral vasoconstriction syndrome | 77.09 | 38.56 | 18 | 2007 | 4112 | 90622310 |
| Dyspepsia | 76.15 | 38.56 | 50 | 1975 | 198110 | 90428312 |
| Cough | 60.10 | 38.56 | 56 | 1969 | 368906 | 90257516 |
| Ergot poisoning | 57.89 | 38.56 | 8 | 2017 | 87 | 90626335 |
| Drug ineffective | 56.92 | 38.56 | 106 | 1919 | 1384192 | 89242230 |
| Weight decreased | 54.92 | 38.56 | 54 | 1971 | 379856 | 90246566 |
| Abdominal pain | 53.06 | 38.56 | 54 | 1971 | 395667 | 90230755 |
| Nausea | 46.67 | 38.56 | 86 | 1939 | 1110230 | 89516192 |
| Off label use | 44.58 | 38.56 | 84 | 1941 | 1102168 | 89524254 |
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Nightmare | 840.51 | 630.28 | 190 | 1340 | 24822 | 42594983 |
| Sedation | 803.15 | 630.28 | 190 | 1340 | 30285 | 42589520 |
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Nightmare | 755.10 | 55.09 | 185 | 3197 | 38678 | 110547239 |
| Sedation | 652.49 | 55.09 | 186 | 3196 | 69497 | 110516420 |
| Nephrolithiasis | 531.70 | 55.09 | 157 | 3225 | 66055 | 110519862 |
| Hyperhidrosis | 479.07 | 55.09 | 188 | 3194 | 187110 | 110398807 |
| Product use in unapproved indication | 293.85 | 55.09 | 177 | 3205 | 447200 | 110138717 |
| Neovascularisation | 292.79 | 55.09 | 50 | 3332 | 1687 | 110584230 |
| Drug ineffective | 288.84 | 55.09 | 286 | 3096 | 1520254 | 109065663 |
| Nausea | 240.09 | 55.09 | 236 | 3146 | 1235454 | 109350463 |
| Off label use | 222.61 | 55.09 | 248 | 3134 | 1499937 | 109085980 |
| Paradoxical drug reaction | 206.43 | 55.09 | 50 | 3332 | 9767 | 110576150 |
| Anuria | 161.47 | 55.09 | 50 | 3332 | 24291 | 110561626 |
| Extrapyramidal disorder | 161.22 | 55.09 | 52 | 3330 | 28815 | 110557102 |
| Product used for unknown indication | 144.24 | 55.09 | 28 | 3354 | 1935 | 110583982 |
| Treatment failure | 124.97 | 55.09 | 87 | 3295 | 277147 | 110308770 |
| Drug ineffective for unapproved indication | 103.06 | 55.09 | 54 | 3328 | 102784 | 110483133 |
| Reversible cerebral vasoconstriction syndrome | 64.11 | 55.09 | 17 | 3365 | 4744 | 110581173 |
| Dyspepsia | 61.34 | 55.09 | 49 | 3333 | 190916 | 110395001 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | N02CA01 | NERVOUS SYSTEM ANALGESICS ANTIMIGRAINE PREPARATIONS Ergot alkaloids |
| ATC | N02CA51 | NERVOUS SYSTEM ANALGESICS ANTIMIGRAINE PREPARATIONS Ergot alkaloids |
| FDA CS | M0007665 | Ergotamines |
| MeSH PA | D000700 | Analgesics |
| MeSH PA | D002317 | Cardiovascular Agents |
| MeSH PA | D014662 | Vasoconstrictor Agents |
| MeSH PA | D015259 | Dopamine Agents |
| MeSH PA | D018377 | Neurotransmitter Agents |
| MeSH PA | D018491 | Dopamine Agonists |
| MeSH PA | D018689 | Sensory System Agents |
| MeSH PA | D018712 | Analgesics, Non-Narcotic |
| CHEBI has role | CHEBI:35481 | non-narcotic analgesic |
| CHEBI has role | CHEBI:35941 | serotonergic agonist |
| CHEBI has role | CHEBI:50514 | vasoconstrictor agent |
| CHEBI has role | CHEBI:51065 | dopamine agonist |
| CHEBI has role | CHEBI:66991 | sympatholytic agent |
| FDA EPC | N0000175766 | Ergotamine Derivative |
Related Drugs by ATC class:
N02CA Ergot alkaloids 3 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Migraine | indication | 37796009 | DOID:6364 |
| Vascular headache | indication | 128187005 | |
| Cluster headache syndrome | indication | 193031009 | |
| Bacterial septicemia | contraindication | 10001005 | DOID:0040085 |
| Vascular surgery procedure | contraindication | 30904006 | |
| Hypertensive disorder | contraindication | 38341003 | DOID:10763 |
| Acute nephropathy | contraindication | 58574008 | |
| Hepatic failure | contraindication | 59927004 | |
| Prinzmetal angina | contraindication | 87343002 | |
| Pregnancy, function | contraindication | 289908002 | |
| Cardiovascular event risk | contraindication | 395112001 | |
| Peripheral vascular disease | contraindication | 400047006 | |
| Breastfeeding (mother) | contraindication | 413712001 | |
| Disorder of coronary artery | contraindication | 414024009 | |
| Porphyria | contraindication | 418470004 | |
| Hypertensive urgency | contraindication | 443482000 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 11.58 | acidic |
| pKa2 | 12.7 | acidic |
| pKa3 | 13.43 | acidic |
| pKa4 | 7.56 | Basic |
Orange Book patent data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Patent number | Patent expiration date | Patent use |
|---|---|---|---|---|---|---|---|---|---|---|
| 0.725MG/SPRAY | TRUDHESA | IMPEL PHARMS | N213436 | Sept. 2, 2021 | RX | SPRAY, METERED | NASAL | 9919117 | March 17, 2033 | NASAL ADMINISTRATION OF DIHYDROERGOTAMINE MESYLATE BY METERED SPRAY FOR THE ACUTE TREATMENT OF MIGRAINE WITH OR WITHOUT AURA |
| 0.725MG/SPRAY | TRUDHESA | IMPEL PHARMS | N213436 | Sept. 2, 2021 | RX | SPRAY, METERED | NASAL | 11185497 | Jan. 4, 2039 | NASAL ADMINISTRATION OF DIHYDROERGOTAMINE MESYLATE BY METERED SPRAY FOR THE ACUTE TREATMENT OF MIGRAINE WITH OR WITHOUT AURA |
| 1MG/ML | BREKIYA (AUTOINJECTOR) | AMNEAL | N215400 | May 14, 2025 | RX | SOLUTION | SUBCUTANEOUS | 11819501 | Feb. 26, 2039 | ACUTE TREATMENT OF CLUSTER HEADACHES |
| 1MG/ML | BREKIYA (AUTOINJECTOR) | AMNEAL | N215400 | May 14, 2025 | RX | SOLUTION | SUBCUTANEOUS | 11819501 | Feb. 26, 2039 | ACUTE TREATMENT OF MIGRAINE WITH OR WITHOUT AURA |
| 1MG/ML | BREKIYA (AUTOINJECTOR) | AMNEAL | N215400 | May 14, 2025 | RX | SOLUTION | SUBCUTANEOUS | 12329749 | May 27, 2039 | ACUTE TREATMENT OF CLUSTER HEADACHES IN ADULTS |
| 1MG/ML | BREKIYA (AUTOINJECTOR) | AMNEAL | N215400 | May 14, 2025 | RX | SOLUTION | SUBCUTANEOUS | 12329749 | May 27, 2039 | ACUTE TREATMENT OF MIGRAINE WITH OR WITHOUT AURA IN ADULTS |
| 1MG/ML | BREKIYA (AUTOINJECTOR) | AMNEAL | N215400 | May 14, 2025 | RX | SOLUTION | SUBCUTANEOUS | 11083712 | June 30, 2039 | ACUTE TREATMENT OF CLUSTER HEADACHES IN ADULTS |
| 1MG/ML | BREKIYA (AUTOINJECTOR) | AMNEAL | N215400 | May 14, 2025 | RX | SOLUTION | SUBCUTANEOUS | 11083712 | June 30, 2039 | ACUTE TREATMENT OF MIGRAINE WITH OR WITHOUT AURA IN ADULTS |
Orange Book exclusivity data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Exclusivity date | Description |
|---|---|---|---|---|---|---|---|---|---|
| EQ 5.2MG BASE | ATZUMI | SATSUMA PHARMS | N217901 | April 30, 2025 | RX | POWDER | NASAL | April 30, 2028 | NEW PRODUCT |
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| 5-hydroxytryptamine receptor 1D | GPCR | AGONIST | Ki | 9.90 | IUPHAR | CHEMBL | |||
| Mu-type opioid receptor | GPCR | Ki | 6.81 | CHEMBL | |||||
| D(1A) dopamine receptor | GPCR | Ki | 5.92 | DRUG MATRIX | |||||
| D(2) dopamine receptor | GPCR | Ki | 8.53 | DRUG MATRIX | |||||
| Alpha-2A adrenergic receptor | GPCR | Ki | 9.41 | DRUG MATRIX | |||||
| Sigma non-opioid intracellular receptor 1 | Membrane receptor | Ki | 6.22 | CHEMBL | |||||
| Cytochrome P450 3A4 | Enzyme | IC50 | 5.30 | DRUG MATRIX | |||||
| 5-hydroxytryptamine receptor 1A | GPCR | Ki | 9.42 | DRUG MATRIX | |||||
| 5-hydroxytryptamine receptor 2A | GPCR | Ki | 8.64 | DRUG MATRIX | |||||
| 5-hydroxytryptamine receptor 2B | GPCR | Ki | 8.36 | DRUG MATRIX | |||||
| 5-hydroxytryptamine receptor 2C | GPCR | Ki | 7.33 | DRUG MATRIX | |||||
| 5-hydroxytryptamine receptor 6 | GPCR | Ki | 8.83 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 7 | GPCR | ANTAGONIST | Ki | 8 | IUPHAR | ||||
| Alpha-1A adrenergic receptor | GPCR | Ki | 7.48 | CHEMBL | |||||
| Alpha-2B adrenergic receptor | GPCR | Ki | 8.75 | DRUG MATRIX | |||||
| D(3) dopamine receptor | GPCR | Ki | 8.74 | DRUG MATRIX | |||||
| D(1B) dopamine receptor | GPCR | Ki | 5.53 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 1B | GPCR | AGONIST | Ki | 9.20 | IUPHAR | ||||
| Alpha-2C adrenergic receptor | GPCR | Ki | 8.82 | DRUG MATRIX | |||||
| D(4) dopamine receptor | GPCR | Ki | 7.48 | CHEMBL | |||||
| Alpha-1D adrenergic receptor | GPCR | Ki | 8.69 | DRUG MATRIX | |||||
| Alpha-1B adrenergic receptor | GPCR | Ki | 6.92 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 5A | GPCR | Ki | 7.50 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 1F | GPCR | AGONIST | Ki | 7.10 | IUPHAR | ||||
| 5-hydroxytryptamine receptor 1E | GPCR | AGONIST | Ki | 5.60 | IUPHAR | ||||
| Solute carrier family 22 member 2 | Transporter | IC50 | 4.30 | CHEMBL | |||||
| Multidrug and toxin extrusion protein 1 | Transporter | IC50 | 5.55 | CHEMBL | |||||
| Multidrug and toxin extrusion protein 2 | Transporter | IC50 | 4.90 | CHEMBL | |||||
| Transmembrane protein 97 | Enzyme | Ki | 5.55 | CHEMBL | |||||
| Alpha-1B adrenergic receptor | GPCR | Ki | 8.35 | DRUG MATRIX | |||||
| 5-hydroxytryptamine receptor 1B | GPCR | Ki | 9.42 | DRUG MATRIX | |||||
| Alpha-1A adrenergic receptor | GPCR | IC50 | 8.30 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 1A | GPCR | IC50 | 9.18 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 7 | GPCR | ANTAGONIST | Ki | 6.80 | IUPHAR | ||||
| Gastrin/cholecystokinin type B receptor | GPCR | IC50 | 4.64 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 6 | GPCR | ANTAGONIST | Ki | 8.30 | IUPHAR | ||||
| Adrenergic receptor alpha-2 | GPCR | IC50 | 8.43 | CHEMBL | |||||
| 5-hydroxytryptamine receptor 4 | GPCR | Ki | 6.80 | DRUG MATRIX |
External reference:
| ID | Source |
|---|---|
| D02211 | KEGG_DRUG |
| 5989-77-5 | SECONDARY_CAS_RN |
| 6190-39-2 | SECONDARY_CAS_RN |
| 203176 | RXNORM |
| 4018754 | VANDF |
| 4019721 | VANDF |
| C0012291 | UMLSCUI |
| CHEBI:4562 | CHEBI |
| 2GM | PDB_CHEM_ID |
| CHEMBL1732 | ChEMBL_ID |
| CHEMBL1200517 | ChEMBL_ID |
| D004087 | MESH_DESCRIPTOR_UI |
| DB00320 | DRUGBANK_ID |
| 121 | IUPHAR_LIGAND_ID |
| 2022 | INN_ID |
| 436O5HM03C | UNII |
| 10531 | PUBCHEM_CID |
| 4600 | MMSL |
| 47279 | MMSL |
| d00211 | MMSL |
| 000679 | NDDF |
| 004529 | NDDF |
| 006588 | NDDF |
| 387267005 | SNOMEDCT_US |
| 387468003 | SNOMEDCT_US |
| 48875009 | SNOMEDCT_US |
| 436O5HM03C | INXIGHT DRUGS |
Pharmaceutical products:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| Dihydroergotamine Mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0143-9151 | INJECTION | 1 mg | INTRAMUSCULAR | ANDA | 22 sections |
| Dihydroergotamine Mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0143-9273 | INJECTION | 1 mg | INTRAMUSCULAR | ANDA | 22 sections |
| Dihydroergotamine Mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 24201-463 | SPRAY | 4 mg | NASAL | ANDA | 22 sections |
| dihydroergotamine mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 36000-300 | INJECTION, SOLUTION | 1 mg | INTRAVENOUS | ANDA | 20 sections |
| BREKIYA | HUMAN PRESCRIPTION DRUG LABEL | 1 | 64896-509 | INJECTION | 1 mg | SUBCUTANEOUS | NDA | 26 sections |
| BREKIYA | HUMAN PRESCRIPTION DRUG LABEL | 1 | 64896-509 | INJECTION | 1 mg | SUBCUTANEOUS | NDA | 26 sections |
| Dihydroergotamine Mesylate | Human Prescription Drug Label | 1 | 68083-466 | INJECTION | 1 mg | INTRAVENOUS | ANDA | 22 sections |
| Dihydroergotamine Mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 68682-357 | SPRAY | 4 mg | NASAL | NDA authorized generic | 28 sections |
| Dihydroergotamine Mesylate Nasal | HUMAN PRESCRIPTION DRUG LABEL | 1 | 69097-503 | SPRAY, METERED | 4 mg | NASAL | ANDA | 19 sections |
| DIHYDROERGOTAMINE MESYLATE | HUMAN PRESCRIPTION DRUG LABEL | 1 | 70069-880 | SPRAY, METERED | 4 mg | NASAL | ANDA | 15 sections |
| Dromelate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 70529-030 | INJECTION, SOLUTION | 1 mg | SUBCUTANEOUS | ANDA | 22 sections |
| Dihydroergotamine Mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 71357-013 | INJECTION, SOLUTION | 1 mg | INTRAVENOUS | ANDA | 24 sections |
| Dihydroergotamine mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 72888-096 | SPRAY | 4 mg | NASAL | ANDA | 15 sections |
| Dihydroergotamine mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 73352-096 | SPRAY | 4 mg | NASAL | ANDA | 16 sections |
| Dihydroergotamine Mesylate Nasal | HUMAN PRESCRIPTION DRUG LABEL | 1 | 76282-680 | SPRAY, METERED | 4 mg | NASAL | ANDA | 18 sections |
| ATZUMI | HUMAN PRESCRIPTION DRUG LABEL | 1 | 76978-101 | POWDER | 5.20 mg | NASAL | NDA | 35 sections |
| Trudhesa | HUMAN PRESCRIPTION DRUG LABEL | 1 | 77530-725 | SPRAY, METERED | 4 mg | NASAL | NDA | 35 sections |
| Dihydroergotamine Mesylate | HUMAN PRESCRIPTION DRUG LABEL | 1 | 81284-411 | INJECTION, SOLUTION | 1 mg | INTRAVENOUS | ANDA | 24 sections |