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dihydroergotamine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
ergot alkaloid derivatives	888	511-12-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: dihydroergotamine mesilate dihydroergotamine tartrate dihydroergotamine 9,10-Dihydroergotamine dihydroergotamine mesylate	A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS. Molecular weight: 583.69 Formula: C33H37N5O5 CLOGP: 4.76 LIPINSKI: 1 HAC: 10 HDO: 3 TPSA: 118.21 ALOGS: -3.41 ROTB: 4 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

dihydroergotamine mesilate
dihydroergotamine tartrate
dihydroergotamine
9,10-Dihydroergotamine
dihydroergotamine mesylate

A 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.

Molecular weight: 583.69
Formula: C33H37N5O5
CLOGP: 4.76
LIPINSKI: 1
HAC: 10
HDO: 3
TPSA: 118.21
ALOGS: -3.41
ROTB: 4

Status: OFP

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:

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Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Bocci G, Oprea TI, Benet LZ
CL (Clearance)	15.07 mL/min/kg	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	1 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	0.55 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.33 L/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.07 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	0.07 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.07 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
April 12, 1946	FDA	VALEANT

FDA Adverse Event Reporting System (Female)

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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	219.26	30.60	36	1646	1109	63486231
Paradoxical drug reaction	172.97	30.60	36	1646	4116	63483224
Extrapyramidal disorder	140.69	30.60	38	1644	13246	63474094
Anuria	133.36	30.60	36	1646	12515	63474825
Drug ineffective for unapproved indication	105.45	30.60	38	1644	34025	63453315
Reversible cerebral vasoconstriction syndrome	76.43	30.60	17	1665	2641	63484699
Dyspepsia	60.19	30.60	36	1646	102160	63385180
Ergot poisoning	56.05	30.60	8	1674	93	63487247
Treatment failure	55.07	30.60	44	1638	198999	63288341
Migraine	35.42	30.60	26	1656	103320	63384020

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FDA Adverse Event Reporting System (Male)

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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	339.41	221.80	73	590	14318	34941950
Sedation	311.91	221.80	73	590	20933	34935335
Nephrolithiasis	290.22	221.80	74	589	30259	34926009
Hyperhidrosis	223.31	221.80	74	589	75618	34880650

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FDA Adverse Event Reporting System (Geriatric)

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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	216.05	38.74	36	2084	1209	79741059
Nightmare	214.17	38.74	61	2059	25800	79716468
Nephrolithiasis	182.22	38.74	64	2056	53227	79689041
Sedation	176.19	38.74	62	2058	51833	79690435
Paradoxical drug reaction	153.10	38.74	36	2084	7149	79735119
Product used for unknown indication	135.49	38.74	25	2095	1519	79740749
Extrapyramidal disorder	120.39	38.74	38	2082	22641	79719627
Hyperhidrosis	117.89	38.74	64	2056	151428	79590840
Anuria	114.91	38.74	36	2084	20927	79721341
Drug ineffective for unapproved indication	107.22	38.74	43	2077	51195	79691073

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	N02CA01	NERVOUS SYSTEM ANALGESICS ANTIMIGRAINE PREPARATIONS Ergot alkaloids
ATC	N02CA51	NERVOUS SYSTEM ANALGESICS ANTIMIGRAINE PREPARATIONS Ergot alkaloids
CHEBI has role	CHEBI:35941	serotonin agonists
CHEBI has role	CHEBI:51065	Dopamine receptor agonist
CHEBI has role	CHEBI:66991	sympatholytic drug
FDA CS	M0007665	Ergotamines
FDA EPC	N0000175766	Ergotamine Derivative
MeSH PA	D000700	Analgesics
MeSH PA	D018712	Analgesics, Non-Narcotic
MeSH PA	D002317	Cardiovascular Agents

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

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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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.58	acidic
pKa2	12.7	acidic
pKa3	13.43	acidic
pKa4	7.56	Basic

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Orange Book patent data (new drug applications)

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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

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
0.725MG/SPRAY	TRUDHESA	IMPEL PHARMS	N213436	Sept. 2, 2021	RX	SPRAY, METERED	NASAL	Sept. 2, 2024	NEW PRODUCT

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
5-hydroxytryptamine receptor 1D	GPCR	P28221	5HT1D_HUMAN	AGONIST	Ki	9.90	IUPHAR	CHEMBL
D(1A) dopamine receptor	GPCR	P21728	DRD1_HUMAN		Ki	5.92	DRUG MATRIX
D(2) dopamine receptor	GPCR	P14416	DRD2_HUMAN		Ki	8.53	DRUG MATRIX
Alpha-2A adrenergic receptor	GPCR	P08913	ADA2A_HUMAN		Ki	9.41	DRUG MATRIX
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	5.30	DRUG MATRIX
5-hydroxytryptamine receptor 1A	GPCR	P08908	5HT1A_HUMAN		Ki	9.42	DRUG MATRIX
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		Ki	8.64	DRUG MATRIX
5-hydroxytryptamine receptor 2B	GPCR	P41595	5HT2B_HUMAN		Ki	8.36	DRUG MATRIX
5-hydroxytryptamine receptor 2C	GPCR	P28335	5HT2C_HUMAN		Ki	7.33	DRUG MATRIX
5-hydroxytryptamine receptor 6	GPCR	P50406	5HT6R_HUMAN		Ki	8.83	CHEMBL

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External reference:

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ID	Source
2GM	PDB_CHEM_ID
000679	NDDF
004529	NDDF
006588	NDDF
10531	PUBCHEM_CID
121	IUPHAR_LIGAND_ID
2022	INN_ID
203176	RXNORM
387267005	SNOMEDCT_US
387468003	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
D.H.E. 45	HUMAN PRESCRIPTION DRUG LABEL	1	66490-041	INJECTION, SOLUTION	1 mg	INTRAVENOUS	NDA	25 sections
D.H.E. 45	HUMAN PRESCRIPTION DRUG LABEL	1	66490-041	INJECTION, SOLUTION	1 mg	INTRAVENOUS	NDA	25 sections
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	0143-9273	INJECTION	1 mg	INTRAMUSCULAR	ANDA	22 sections
Dihydroergotamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	0574-0850	INJECTION, SOLUTION	1 mg	SUBCUTANEOUS	ANDA	24 sections
Dihydroergotamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	0574-0850	INJECTION, SOLUTION	1 mg	SUBCUTANEOUS	ANDA	24 sections
Dihydroergotamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	24201-463	SPRAY	4 mg	NASAL	ANDA	28 sections
Dihydroergotamine Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	24201-463	SPRAY	4 mg	NASAL	ANDA	28 sections
dihydroergotamine mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	25021-609	INJECTION, SOLUTION	1 mg	INTRAVENOUS	ANDA	25 sections

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