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Chemistry

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Also known as: Dantrolene sodium, 14663-23-1, Tox21_500424, Ccg-221728, Ncgc00261109-01, Ac-25752
Molecular Formula
C14H9N4NaO5
Molecular Weight
336.23  g/mol
InChI Key
KSRLIXGNPXAZHD-HAZZGOGXSA-M

Dantrolene
Skeletal muscle relaxant that acts by interfering with excitation-contraction coupling in the muscle fiber. It is used in spasticity and other neuromuscular abnormalities. Although the mechanism of action is probably not central, dantrolene is usually grouped with the central muscle relaxants.
1 2D Structure

Dantrolene

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;1-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidin-3-ide-2,4-dione
2.1.2 InChI
InChI=1S/C14H10N4O5.Na/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22;/h1-7H,8H2,(H,16,19,20);/q;+1/p-1/b15-7+;
2.1.3 InChI Key
KSRLIXGNPXAZHD-HAZZGOGXSA-M
2.1.4 Canonical SMILES
C1C(=O)[N-]C(=O)N1N=CC2=CC=C(O2)C3=CC=C(C=C3)[N+](=O)[O-].[Na+]
2.1.5 Isomeric SMILES
C1C(=O)[N-]C(=O)N1/N=C/C2=CC=C(O2)C3=CC=C(C=C3)[N+](=O)[O-].[Na+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Dantrium

2. Dantrolene

3. Dantrolene Sodium

4. Sodium, Dantrolene

2.2.2 Depositor-Supplied Synonyms

1. Dantrolene Sodium

2. 14663-23-1

3. Tox21_500424

4. Ccg-221728

5. Ncgc00261109-01

6. Ac-25752

7. D 9175

2.3 Create Date
2007-02-08
3 Chemical and Physical Properties
Molecular Weight 336.23 g/mol
Molecular Formula C14H9N4NaO5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass336.04706368 g/mol
Monoisotopic Mass336.04706368 g/mol
Topological Polar Surface Area110 Ų
Heavy Atom Count24
Formal Charge0
Complexity530
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDantrolene sodium
Drug LabelThe chemical formula of dantrolene sodium is hydrated 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2, 4-imidazolidinedione sodium salt. It is an orange powder, slightly soluble in water, but due to its slightly acidic nature the solubility incre...
Active IngredientDantrolene sodium
Dosage FormCapsule
RouteOral
Strength100mg; 25mg; 50mg
Market StatusPrescription
CompanyMikah Pharma; Impax Labs

2 of 2  
Drug NameDantrolene sodium
Drug LabelThe chemical formula of dantrolene sodium is hydrated 1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2, 4-imidazolidinedione sodium salt. It is an orange powder, slightly soluble in water, but due to its slightly acidic nature the solubility incre...
Active IngredientDantrolene sodium
Dosage FormCapsule
RouteOral
Strength100mg; 25mg; 50mg
Market StatusPrescription
CompanyMikah Pharma; Impax Labs

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Muscle Relaxants, Central

A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Decreased Striated Muscle Tone [PE]; Skeletal Muscle Relaxant [EPC]; Decreased Striated Muscle Contraction [PE]

NDC API

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01

Medlab Asia & Asia Health
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Medlab Asia & Asia Health
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DANTROLENE SODIUM

NDC Package Code : 69575-4036

Start Marketing Date : 2021-10-29

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (30kg/30kg)

Marketing Category : BULK INGREDIENT

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02

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

NDC Package Code : 69988-0029

Start Marketing Date : 2006-09-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/1)

Marketing Category : DRUG FOR FURTHER PROCESSING

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03

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

NDC Package Code : 71052-508

Start Marketing Date : 2019-08-05

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (500g/500g)

Marketing Category : BULK INGREDIENT

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04

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

NDC Package Code : 67262-2000

Start Marketing Date : 2007-10-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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05

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

NDC Package Code : 65129-1012

Start Marketing Date : 2002-01-10

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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06

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

NDC Package Code : 49452-2440

Start Marketing Date : 2016-05-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1g/g)

Marketing Category : BULK INGREDIENT

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API Reference Price

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ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q1","strtotime":1646245800,"product":"DANTROLENE SODIUM","address":"Part of Plot No.11 & 87, Sy No.119 Phase - IV, Extension in IP, Pasham","city":"HYDERABAD","supplier":"SCINOPHARM TAIWAN, LTD","supplierCountry":"TAIWAN","foreign_port":"NA","customer":"GLAND PHARMA LIMITED","customerCountry":"INDIA","quantity":"0.12","actualQuantity":"0.12","unit":"KGS","unitRateFc":"4833.3","totalValueFC":"578.7","currency":"USD","unitRateINR":"367575","date":"03-Mar-2022","totalValueINR":"44109","totalValueInUsd":"578.7","indian_port":"HYDERABAD AIR","hs_no":"29339990","bill_no":"7716799","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"Part of Plot No.11 & 87, Sy No.119 Phase - IV, Extension in IP, Pasham"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q1","strtotime":1646332200,"product":"DANTROLENE SODIUM (AS PER TEST LIC.TL\/BDZ\/21\/000310 DT.14\/12\/2021)","address":"VILLAGE THANTHEWAL ROPAR ROAD NALAGARH","city":"DISTT SOLAN","supplier":"SCINOPHARM TAIWAN, LTD","supplierCountry":"TAIWAN","foreign_port":"NA","customer":"IMMACULE LIFESCIENCES P. 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Vandalur Main Road Pudupakkam"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q2","strtotime":1681324200,"product":"DANTROLENE SODIUM 3700688 LOT NO. 70330AA134 \/ 70330AA137 CAS.NO.24868-20-0","address":"No. 9\/215, Pudupakkam - Vandalur Main Road Pudupakkam","city":"Kelambakkam","supplier":"BIDDLE SAWYER CORPORATION","supplierCountry":"TAIWAN","foreign_port":"NA","customer":"PAR PHARMACEUTICAL","customerCountry":"INDIA","quantity":"59.35","actualQuantity":"59.35","unit":"KGS","unitRateFc":"2300","totalValueFC":"137997.8","currency":"USD","unitRateINR":"190555","date":"13-Apr-2023","totalValueINR":"11309439.25","totalValueInUsd":"137997.8","indian_port":"MADRAS AIR","hs_no":"29349990","bill_no":"5497231","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"No. 9\/215, Pudupakkam - Vandalur Main Road Pudupakkam"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1708885800,"product":"DANTROLENE SODIUM","address":"882\/1-871, NEAR KANKAVATI ,VILLAGE-","city":"AHMEDABAD, GUJARAT","supplier":"SCINOPHARM TAIWAN, LTD","supplierCountry":"TAIWAN","foreign_port":"TAIPEI","customer":"AMNEAL PHARMACEUTICALS","customerCountry":"INDIA","quantity":"26.00","actualQuantity":"26","unit":"KGS","unitRateFc":"2237","totalValueFC":"58811.8","currency":"USD","unitRateINR":"187685.9","date":"26-Feb-2024","totalValueINR":"4879834","totalValueInUsd":"58811.8","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29349990","bill_no":"1000748","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"TAIPEI","supplierAddress":"N\/A","customerAddress":"882\/1-871, NEAR KANKAVATI ,VILLAGE-"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1715193000,"product":"DANTROLENE SODIUM LOT NO. 70330AA143 CAS.NO.24868-20-0","address":"OLD NO.1\/63, NEW NO.1\/58 PUDUPAKKAM","city":"","supplier":"BIDDLE SAWYER CORPORATION","supplierCountry":"TAIWAN","foreign_port":"TAIPEI","customer":"PAR PHARMACEUTICAL","customerCountry":"INDIA","quantity":"88.95","actualQuantity":"88.95","unit":"KGS","unitRateFc":"2250","totalValueFC":"202528.5","currency":"USD","unitRateINR":"189787.5","date":"09-May-2024","totalValueINR":"16881598.13","totalValueInUsd":"202528.5","indian_port":"Madras Air","hs_no":"29349990","bill_no":"3396890","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"TAIPEI","supplierAddress":"505 EIGHTH AVENUE,NEW YORK NY 10018SDNF UNITED STATES","customerAddress":"OLD NO.1\/63, NEW NO.1\/58 PUDUPAKKAM"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729794600,"product":"DANTROLENE SODIUM (BATCH NO: 70330AA141) DANTROLENE SODIUM (BATCH NO: 70330AA141)","address":"882\/1-871, NEAR KANKAVATI ,VILLAGE-","city":"AHMEDABAD, GUJARAT","supplier":"SCINOPHARM TAIWAN, LTD","supplierCountry":"TAIWAN","foreign_port":"KAOHSIUNG","customer":"AMNEAL PHARMACEUTICALS","customerCountry":"INDIA","quantity":"50.10","actualQuantity":"50.1","unit":"KGS","unitRateFc":"2250","totalValueFC":"113963.8","currency":"USD","unitRateINR":"191137.5","date":"25-Oct-2024","totalValueINR":"9575988.75","totalValueInUsd":"113963.8","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29349990","bill_no":"6320496","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"KAOHSIUNG","supplierAddress":"NO.1 , NAN KE 8TH ROAD, SHAN HUA TAINAN 741014 TW","customerAddress":"882\/1-871, NEAR KANKAVATI ,VILLAGE-"}]
07-Jan-2021
25-Oct-2024
KGS
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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(USD/KGS)
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Drugs in Development

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Details:

NPJ5008 (dantrolene sodium hemiheptahydrate) is a RYR1 inhibitor, small molecule drug candidate. It is being evaluated for the treatment of malignant hyperthermia.


Lead Product(s): Dantrolene

Therapeutic Area: Musculoskeletal Brand Name: NPJ5008

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 26, 2024

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01

Norgine

Netherlands
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Medlab Asia & Asia Health
Not Confirmed

Norgine

Netherlands
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Medlab Asia & Asia Health
Not Confirmed

Details : NPJ5008 (dantrolene sodium hemiheptahydrate) is a RYR1 inhibitor, small molecule drug candidate. It is being evaluated for the treatment of malignant hyperthermia.

Brand Name : NPJ5008

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 26, 2024

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Details:

The accelerated share repurchase program will support Eagle's multiple anticipated and ongoing drug development activities which include RYANODEX franchise, anticipated near-term launch of vasopressin, and three potential oncology launches PEMFEXY, fulvestrant and SM-88.


Lead Product(s): Dantrolene

Therapeutic Area: Musculoskeletal Brand Name: Ryanodex

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: JPMorgan Chase Bank

Deal Size: $160.0 million Upfront Cash: Undisclosed

Deal Type: Financing September 24, 2020

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02

Medlab Asia & Asia Health
Not Confirmed
Medlab Asia & Asia Health
Not Confirmed

Details : The accelerated share repurchase program will support Eagle's multiple anticipated and ongoing drug development activities which include RYANODEX franchise, anticipated near-term launch of vasopressin, and three potential oncology launches PEMFEXY, fulve...

Brand Name : Ryanodex

Molecule Type : Small molecule

Upfront Cash : Undisclosed

September 24, 2020

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Details:

The article reported results from an academic-based study that demonstrated dantrolene sodium administered intranasally improved both memory and cognition in a mouse model of Alzheimer’s disease. Eagle markets a formulation of dantrolene sodium but did not sponsor the study.


Lead Product(s): Dantrolene

Therapeutic Area: Neurology Brand Name: Ryanodex

Study Phase: PreclinicalProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable August 19, 2020

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03

Medlab Asia & Asia Health
Not Confirmed
Medlab Asia & Asia Health
Not Confirmed

Details : The article reported results from an academic-based study that demonstrated dantrolene sodium administered intranasally improved both memory and cognition in a mouse model of Alzheimer’s disease. Eagle markets a formulation of dantrolene sodium but did...

Brand Name : Ryanodex

Molecule Type : Small molecule

Upfront Cash : Not Applicable

August 19, 2020

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Details:

Eagle is working to increase production of RYANODEX in advance of clinical results and to potentially shorten the supply chain lead time if necessary.


Lead Product(s): Dantrolene

Therapeutic Area: Infections and Infectious Diseases Brand Name: Undisclosed

Study Phase: PreclinicalProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable April 16, 2020

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04

Medlab Asia & Asia Health
Not Confirmed
Medlab Asia & Asia Health
Not Confirmed

Details : Eagle is working to increase production of RYANODEX in advance of clinical results and to potentially shorten the supply chain lead time if necessary.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

April 16, 2020

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  • Deals

Details:

Eagle Pharmaceuticals and the University of Pennsylvania have entered a exclusive worldwide license agreement for the development of dantrolene sodium for treatment of Alzheimer’s disease.


Lead Product(s): Dantrolene

Therapeutic Area: Neurology Brand Name: Undisclosed

Study Phase: PreclinicalProduct Type: Small molecule

Sponsor: Eagle Pharmaceuticals

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Licensing Agreement January 13, 2020

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05

University of Pennsylvania

Country
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Medlab Asia & Asia Health
Not Confirmed

University of Pennsylvania

Country
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Medlab Asia & Asia Health
Not Confirmed

Details : Eagle Pharmaceuticals and the University of Pennsylvania have entered a exclusive worldwide license agreement for the development of dantrolene sodium for treatment of Alzheimer’s disease.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Undisclosed

January 13, 2020

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  • Deals

Details:

Under the terms of the agreement, NorthShore University HealthSystem will study Eagle’s RYANODEX® (dantrolene sodium) for traumatic brain injury (TBI) in animal models.


Lead Product(s): Dantrolene

Therapeutic Area: Trauma (Emergency, Injury, Surgery) Brand Name: Undisclosed

Study Phase: UndisclosedProduct Type: Small molecule

Sponsor: Eagle Pharmaceuticals

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Agreement January 06, 2020

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06

NorthShore University HealthSystem

Country
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Medlab Asia & Asia Health
Not Confirmed

NorthShore University HealthSystem

Country
arrow
Medlab Asia & Asia Health
Not Confirmed

Details : Under the terms of the agreement, NorthShore University HealthSystem will study Eagle’s RYANODEX® (dantrolene sodium) for traumatic brain injury (TBI) in animal models.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Undisclosed

January 06, 2020

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FDA Orange Book

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01

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTROLENE SODIUM

Dosage Form : INJECTABLE;INJECTION

Dosage Strength : 20MG/VIAL

Approval Date : 2016-02-18

Application Number : 205239

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

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02

EAGLE PHARMS

U.S.A
Medlab Asia & Asia Health
Not Confirmed
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EAGLE PHARMS

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : RYANODEX

Dosage Form : FOR SUSPENSION;INTRAVENOUS

Dosage Strength : 250MG/VIAL

Approval Date : 2014-07-22

Application Number : 205579

RX/OTC/DISCN : RX

RLD : Yes

TE Code :

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03

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTROLENE SODIUM

Dosage Form : CAPSULE;ORAL

Dosage Strength : 25MG

Approval Date : 2005-10-24

Application Number : 76686

RX/OTC/DISCN : RX

RLD : No

TE Code : AB

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04

Medlab Asia & Asia Health
Not Confirmed
arrow
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Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTROLENE SODIUM

Dosage Form : CAPSULE;ORAL

Dosage Strength : 50MG

Approval Date : 2005-10-24

Application Number : 76686

RX/OTC/DISCN : RX

RLD : No

TE Code : AB

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05

Medlab Asia & Asia Health
Not Confirmed
arrow
arrow
Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTROLENE SODIUM

Dosage Form : CAPSULE;ORAL

Dosage Strength : 100MG

Approval Date : 2005-10-24

Application Number : 76686

RX/OTC/DISCN : RX

RLD : No

TE Code : AB

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06

HIKMA

United Kingdom
Medlab Asia & Asia Health
Not Confirmed
arrow

HIKMA

United Kingdom
arrow
Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTROLENE SODIUM

Dosage Form : INJECTABLE;INJECTION

Dosage Strength : 20MG/VIAL

Approval Date : 2017-06-19

Application Number : 204762

RX/OTC/DISCN : RX

RLD : No

TE Code : AP

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07

IMPAX LABS

U.S.A
Medlab Asia & Asia Health
Not Confirmed
arrow

IMPAX LABS

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTROLENE SODIUM

Dosage Form : CAPSULE;ORAL

Dosage Strength : 25MG

Approval Date : 2005-03-01

Application Number : 76856

RX/OTC/DISCN : RX

RLD : No

TE Code : AB

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08

IMPAX LABS

U.S.A
Medlab Asia & Asia Health
Not Confirmed
arrow

IMPAX LABS

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTROLENE SODIUM

Dosage Form : CAPSULE;ORAL

Dosage Strength : 50MG

Approval Date : 2005-03-01

Application Number : 76856

RX/OTC/DISCN : RX

RLD : No

TE Code : AB

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09

USWM

U.S.A
Medlab Asia & Asia Health
Not Confirmed
arrow

USWM

U.S.A
arrow
Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : REVONTO

Dosage Form : INJECTABLE;INJECTION

Dosage Strength : 20MG/VIAL

Approval Date : 2007-07-24

Application Number : 78378

RX/OTC/DISCN : RX

RLD : No

TE Code : AP

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10

ENDO OPERATIONS

Country
Medlab Asia & Asia Health
Not Confirmed
arrow

ENDO OPERATIONS

Country
arrow
Medlab Asia & Asia Health
Not Confirmed

DANTROLENE SODIUM

Brand Name : DANTRIUM

Dosage Form : CAPSULE;ORAL

Dosage Strength : 25MG

Approval Date : 1982-01-01

Application Number : 17443

RX/OTC/DISCN : RX

RLD : Yes

TE Code : AB

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CAPSULE;ORAL - 100MG

USFDA APPLICATION NUMBER - 17443

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DOSAGE - CAPSULE;ORAL - 25MG

USFDA APPLICATION NUMBER - 17443

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DOSAGE - CAPSULE;ORAL - 50MG

USFDA APPLICATION NUMBER - 17443

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