Identification
NameHydroxyurea
Accession NumberDB01005  (APRD00023)
TypeSmall Molecule
GroupsApproved
Description

An antineoplastic agent that inhibits DNA synthesis through the inhibition of ribonucleoside diphosphate reductase. [PubChem]

Structure
Thumb
Synonyms
Carbamohydroxamic Acid
Carbamohydroximic Acid
Carbamoyl Oxime
Carbamyl Hydroxamate
Hidroxicarbamida
Hydrea
Hydroxycarbamid
Hydroxycarbamide
Hydroxycarbamidum
Hydroxyharnstoff
Hydroxyurea
N-Carbamoylhydroxylamine
N-Hydroxyurea
Oxyurea
External IDs NSC-32065 / SQ 1089 / SQ-1089
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DroxiaCapsule400 mg/1OralE.R. Squibb & Sons, L.L.C.2009-06-01Not applicableUs
DroxiaCapsule200 mg/1OralE.R. Squibb & Sons, L.L.C.2009-06-01Not applicableUs
DroxiaCapsule300 mg/1OralE.R. Squibb & Sons, L.L.C.2009-06-01Not applicableUs
HydreaCapsule500 mg/1OralE.R. Squibb & Sons, L.L.C.2009-06-01Not applicableUs
Hydrea Cap 500mgCapsule500 mgOralBristol Myers Squibb1979-12-31Not applicableCanada
HydroxyureaCapsule500 mgOralSanis Health Inc2010-02-25Not applicableCanada
Mylan-hydroxyureaCapsule500 mgOralMylan Pharmaceuticals2001-02-22Not applicableCanada
SiklosTablet, film coated100 mgOralAddmedica2007-06-29Not applicableEu
SiklosTablet, film coated100 mgOralAddmedica2007-06-29Not applicableEu
SiklosTablet, film coated1000 mgOralAddmedica2007-06-29Not applicableEu
SiklosTablet, film coated100 mgOralAddmedica2007-06-29Not applicableEu
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-hydroxyureaCapsule500 mgOralApotex Corporation2003-10-22Not applicableCanada
HydroxyureaCapsule500 mg/1OralAv Kare, Inc.2013-07-19Not applicableUs
HydroxyureaCapsule500 mg/1OralAmerincan Health Packaging2008-08-12Not applicableUs
HydroxyureaCapsule500 mg/1OralPhysicians Total Care, Inc.2003-04-11Not applicableUs
HydroxyureaCapsule500 mg/1OralTeva1998-10-19Not applicableUs
HydroxyureaCapsule500 mg/1OralCardinal Health2008-08-12Not applicableUs
HydroxyureaCapsule500 mg/1OralGolden State Medical Supply1999-02-24Not applicableUs
HydroxyureaCapsule500 mg/1OralPar Pharmaceutical1999-02-24Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
LitalirBristol-Myers Squibb
Onco-CarbideTeofarma
Brand mixturesNot Available
Categories
UNIIX6Q56QN5QC
CAS number127-07-1
WeightAverage: 76.0547
Monoisotopic: 76.027277382
Chemical FormulaCH4N2O2
InChI KeyVSNHCAURESNICA-UHFFFAOYSA-N
InChI
InChI=1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)
IUPAC Name
hydroxyurea
SMILES
NC(=O)NO
Pharmacology
Indication

For management of melanoma, resistant chronic myelocytic leukemia, and recurrent, metastatic, or inoperable carcinoma of the ovary and Sickle-cell anemia.

Structured Indications
Pharmacodynamics

Hydroxyurea has dose-dependent synergistic activity with cisplatin in vitro. In vivo Hydroxyurea showed activity in combination with cisplatin against the LX-1 and CALU-6 human lung xenografts, but minimal activity was seen with the NCI-H460 or NCI-H520 xenografts. Hydroxyurea was synergistic with cisplatin in the Lewis lung murine xenograft. Sequential exposure to Hydroxyurea 4 hours before cisplatin produced the greatest interaction.

Mechanism of action

Hydroxyurea is converted to a free radical nitroxide (NO) in vivo, and transported by diffusion into cells where it quenches the tyrosyl free radical at the active site of the M2 protein subunit of ribonucleotide reductase, inactivating the enzyme. The entire replicase complex, including ribonucleotide reductase, is inactivated and DNA synthesis is selectively inhibited, producing cell death in S phase and synchronization of the fraction of cells that survive. Repair of DNA damaged by chemicals or irradiation is also inhibited by hydroxyurea, offering potential synergy between hydroxyurea and radiation or alkylating agents. Hydroxyurea also increases the level of fetal hemoglobin, leading to a reduction in the incidence of vasoocclusive crises in sickle cell anemia. Levels of fetal hemoglobin increase in response to activation of soluble guanylyl cyclase (sGC) by hydroxyurea-derived NO.

TargetKindPharmacological actionActionsOrganismUniProt ID
Ribonucleoside-diphosphate reductase large subunitProteinyes
inhibitor
HumanP23921 details
Related Articles
Absorption

Well absorbed from the gastrointestinal tract.

Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of elimination

Renal excretion is a pathway of elimination.

Half life

3-4 hours

ClearanceNot Available
Toxicity

Oral, mouse: LD50 = 7330 mg/kg; Oral, rat: LD50 = 5760 mg/kg Teratogenicity: Teratogenic effects have occurred in experimental animals.Hydroxyurea use during a small number of human pregnancies has been reported. Adverse effects have not been observed in any of the exposed newborns. Reproductive Effects: Adverse reproductive effects have occurred in experimental animals. Mutagenicity: Mutagenic effects have occurred in experimental animals.Mutagenic effects have occurred in humans.

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Hydroxyurea.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Hydroxyurea.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Hydroxyurea.Approved
ClozapineThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with Clozapine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Hydroxyurea.Approved, Investigational
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Hydroxyurea.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Hydroxyurea.Approved
DidanosineThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with Didanosine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Hydroxyurea.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Hydroxyurea.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Hydroxyurea.Approved, Investigational
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Hydroxyurea.Approved
FingolimodHydroxyurea may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
G17DTThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with G17DT.Investigational
INGN 201The risk or severity of adverse effects can be increased when Hydroxyurea is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Hydroxyurea is combined with INGN 225.Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with Leflunomide.Approved, Investigational
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Hydroxyurea.Withdrawn
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Hydroxyurea.Approved, Investigational
NatalizumabThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with Natalizumab.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Hydroxyurea.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Hydroxyurea.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Hydroxyurea.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Hydroxyurea.Approved, Investigational
RindopepimutThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with CDX-110.Investigational
RoflumilastRoflumilast may increase the immunosuppressive activities of Hydroxyurea.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Hydroxyurea.Approved
SRP 299The risk or severity of adverse effects can be increased when Hydroxyurea is combined with SRP 299.Investigational
StavudineThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with Stavudine.Approved, Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Hydroxyurea.Approved, Investigational
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Hydroxyurea.Withdrawn
TofacitinibHydroxyurea may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Hydroxyurea.Approved, Investigational
Food Interactions
  • Take without regard to meals. Drink liberally.
References
Synthesis Reference

Dee W. Brooks, Andrew O. Stewart, Richard A. Craig, "Substituted aryl- and heteroarylalkenyl-N-hydroxyurea inhibitors of leukotriene biosynthesis." U.S. Patent US5506261, issued October, 1990.

US5506261
General ReferencesNot Available
External Links
ATC CodesL01XX05
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (75.1 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentSickle Cell Disorders1
0WithdrawnTreatmentPulmonary Hypertension (PH)1
1CompletedNot AvailableSickle Cell Disorders1
1CompletedTreatmentBrain and Central Nervous System Tumors2
1CompletedTreatmentChronic Kidney Disease (CKD) / Pulmonary Hypertension (PH) / Sickle Cell Disorders1
1CompletedTreatmentCongenital Marrow Failures / Haemoglobinopathies congenital / Immunodeficiencies / Inborn Errors of Metabolism / Lysosomal Storage Diseases / Non Malignant Disorders / Sickle Cell / Thalassaemic disorders1
1CompletedTreatmentGlioblastomas / Gliosarcoma2
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
1CompletedTreatmentMetastatic Squamous Neck Cancer With Occult Primary Squamous Cell Carcinoma / Recurrent Adenoid Cystic Carcinoma of the Oral Cavity / Recurrent Basal Cell Carcinoma of the Lip / Recurrent Esthesioneuroblastoma of the Paranasal Sinus and Nasal Cavity / Recurrent Inverted Papilloma of the Paranasal Sinus and Nasal Cavity / Recurrent Lymphoepithelioma of the Nasopharynx / Recurrent Lymphoepithelioma of the Oropharynx / Recurrent Metastatic Squamous Neck Cancer With Occult Primary / Recurrent Midline Lethal Granuloma of the Paranasal Sinus and Nasal Cavity / Recurrent Mucoepidermoid Carcinoma of the Oral Cavity / Recurrent Salivary Gland Cancer / Recurrent Squamous Cell Carcinoma of the Hypopharynx / Recurrent Squamous Cell Carcinoma of the Larynx / Recurrent Squamous Cell Carcinoma of the Lip and Oral Cavity / Recurrent Squamous Cell Carcinoma of the Nasopharynx / Recurrent Squamous Cell Carcinoma of the Oropharynx / Recurrent Squamous Cell Carcinoma of the Paranasal Sinus and Nasal Cavity / Recurrent Verrucous Carcinoma of the Larynx / Recurrent Verrucous Carcinoma of the Oral Cavity / Stage III Adenoid Cystic Carcinoma of the Oral Cavity / Stage III Basal Cell Carcinoma of the Lip / Stage III Esthesioneuroblastoma of the Paranasal Sinus and Nasal Cavity / Stage III Inverted Papilloma of the Paranasal Sinus and Nasal Cavity / Stage III Lymphoepithelioma of the Nasopharynx / Stage III Lymphoepithelioma of the Oropharynx / Stage III Midline Lethal Granuloma of the Paranasal Sinus and Nasal Cavity / Stage III Mucoepidermoid Carcinoma of the Oral Cavity / Stage III Salivary Gland Cancer / Stage III Squamous Cell Carcinoma of the Hypopharynx / Stage III Squamous Cell Carcinoma of the Larynx / Stage III Squamous Cell Carcinoma of the Lip and Oral Cavity / Stage III Squamous Cell Carcinoma of the Nasopharynx / Stage III Squamous Cell Carcinoma of the Oropharynx / Stage III Squamous Cell Carcinoma of the Paranasal Sinus and Nasal Cavity / Stage III Verrucous Carcinoma of the Larynx / Stage III Verrucous Carcinoma of the Oral Cavity / Stage IV Adenoid Cystic Carcinoma of the Oral Cavity / Stage IV Basal Cell Carcinoma of the Lip / Stage IV Esthesioneuroblastoma of the Paranasal Sinus and Nasal Cavity / Stage IV Inverted Papilloma of the Paranasal Sinus and Nasal Cavity / Stage IV Lymphoepithelioma of the Nasopharynx / Stage IV Lymphoepithelioma of the Oropharynx / Stage IV Midline Lethal Granuloma of the Paranasal Sinus and Nasal Cavity / Stage IV Mucoepidermoid Carcinoma of the Oral Cavity / Stage IV Salivary Gland Cancer / Stage IV Squamous Cell Carcinoma of the Hypopharynx / Stage IV Squamous Cell Carcinoma of the Larynx / Stage IV Squamous Cell Carcinoma of the Lip and Oral Cavity / Stage IV Squamous Cell Carcinoma of the Nasopharynx / Stage IV Squamous Cell Carcinoma of the Oropharynx / Stage IV Squamous Cell Carcinoma of the Paranasal Sinus and Nasal Cavity / Stage IV Verrucous Carcinoma of the Larynx / Stage IV Verrucous Carcinoma of the Oral Cavity / Untreated Metastatic Squamous Neck Cancer With Occult Primary1
1CompletedTreatmentSickle Cell Disorders2
1RecruitingTreatmentRecurrent Salivary Gland Cancer / Recurrent Squamous Cell Carcinoma of the Hypopharynx / Recurrent Squamous Cell Carcinoma of the Larynx / Recurrent Squamous Cell Carcinoma of the Lip and Oral Cavity / Recurrent Squamous Cell Carcinoma of the Nasopharynx / Recurrent Squamous Cell Carcinoma of the Oropharynx / Recurrent Squamous Cell Carcinoma of the Paranasal Sinus and Nasal Cavity / Recurrent Verrucous Carcinoma of the Larynx / Recurrent Verrucous Carcinoma of the Oral Cavity / Salivary Gland Squamous Cell Carcinoma / Tongue Cancer1
1Unknown StatusTreatmentLung Cancers1
1WithdrawnTreatmentAdvanced Solid Tumors1
1, 2Active Not RecruitingTreatmentSickle Cell Disorders1
1, 2CompletedTreatmentHead and Neck Carcinoma1
1, 2CompletedTreatmentLeukemia, Myelogenous, Chronic, BCR-ABL Positive1
1, 2CompletedTreatmentMuscular Atrophy, Spinal1
1, 2CompletedTreatmentSickle Cell Disorders1
1, 2RecruitingTreatmentHead and Neck Squamous Cell Carcinoma (HNSCC) / Human Papillomavirus Infections / Salivary Gland Squamous Cell Carcinoma / Stage IVA Hypopharyngeal Squamous Cell Carcinoma / Stage IVA Laryngeal Squamous Cell Carcinoma / Stage IVA Lip and Oral Cavity Squamous Cell Carcinoma / Stage IVA Major Salivary Gland Carcinoma / Stage IVA Nasal Cavity and Paranasal Sinus Squamous Cell Carcinoma / Stage IVA Oropharyngeal Carcinoma / Stage IVA Oropharyngeal Carcinoma AJCC v7 / Stage IVA Oropharyngeal Squamous Cell Carcinoma / Stage IVB Hypopharyngeal Squamous Cell Carcinoma / Stage IVB Laryngeal Squamous Cell Carcinoma / Stage IVB Lip and Oral Cavity Squamous Cell Carcinoma / Stage IVB Major Salivary Gland Carcinoma / Stage IVB Nasal Cavity and Paranasal Sinus Squamous Cell Carcinoma / Stage IVB Oropharyngeal Carcinoma / Stage IVB Oropharyngeal Carcinoma AJCC v7 / Stage IVB Oropharyngeal Squamous Cell Carcinoma / Tongue Carcinoma1
1, 2TerminatedTreatmentPulmonary Hypertension (PH) / Sickle Cell Disorders1
1, 2Unknown StatusTreatmentEsophageal Cancers1
1, 2Unknown StatusTreatmentMuscular Atrophy, Spinal1
2Active Not RecruitingTreatmentAcute Myeloid Leukaemias (AML)1
2Active Not RecruitingTreatmentHuman Papilloma Virus Infection / Stage III Squamous Cell Carcinoma of the Oropharynx / Stage IVA Squamous Cell Carcinoma of the Oropharynx / Stage IVB Squamous Cell Carcinoma of the Oropharynx1
2CompletedTreatmentAdrenoleukodystrophy / Gangliosidosis, GM1 / I-Cell Disease / Leukodystrophy, Globoid Cell / Metachromatic Leukodystrophy / Sandhoffs Disease / Sanfilippo Syndrome / Tay Sachs Disease / Wolman's Disease1
2CompletedTreatmentAdult Meningioma1
2CompletedTreatmentBeta Thalassemia / Haemoglobinopathies congenital1
2CompletedTreatmentBrain Cancer / Cancers / Meningiomas1
2CompletedTreatmentCancer of the Larynx / Cancer of the Oral Cavity / Cancer of the Pharynx / Head and Neck Carcinoma / Nose Neoplasms / Paranasal Sinus Neoplasms1
2CompletedTreatmentEsophageal Cancers / Head and Neck Carcinoma1
2CompletedTreatmentGlioblastomas / Gliosarcoma1
2CompletedTreatmentHaemoglobinopathies congenital / Hematologic Diseases / Sickle Cell Disorders1
2CompletedTreatmentHead and Neck1
2CompletedTreatmentHead and Neck Carcinoma1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
2CompletedTreatmentLeukemias1
2CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentMalignant Neoplasm of Stomach1
2CompletedTreatmentPolycythemia Vera (PV)1
2CompletedTreatmentSickle Cell Disorders1
2CompletedTreatmentStrokes1
2CompletedTreatmentβ-Thalassemia Intermedia1
2Not Yet RecruitingTreatmentThalassemia, Beta1
2RecruitingPreventionSickle Cell Disorders / Strokes1
2RecruitingTreatmentAcute Myeloid Leukaemias (AML) / Hematopoietic Stem Cell Transplant (HSCT) / Myelodysplastic Syndromes (MDS)1
2RecruitingTreatmentAnemia; Sickle-Cell, With Crisis / Sickle Cell Disorders1
2RecruitingTreatmentCentral Retinal Vein Occlusion, Non-Ischemic1
2RecruitingTreatmentCongenital Bone Marrow Failure Syndromes / Hereditary Anemias / Inherited Metabolic Disorders (IMD) / Patients With Sickle Disease Presenting Specific Symptoms / Primary Immunodeficiency Syndromes1
2RecruitingTreatmentEpstein Barr Virus Associated Hodgkin's Lymphoma / Epstein Barr Virus Associated Non Hodgkin's Lymphoma / Post-transplant Lymphoproliferative Disease (PTLD)1
2RecruitingTreatmentHemoglobin SC Disease2
2RecruitingTreatmentSickle Cell Disorders3
2TerminatedPreventionSickle Cell Disorders1
2TerminatedTreatmentEsophageal Cancers1
2TerminatedTreatmentHemoglobin SC Disease1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2TerminatedTreatmentRecurrent Glioblastoma Multiforme (GBM)1
2Unknown StatusTreatmentBrain and Central Nervous System Tumors2
2Unknown StatusTreatmentCarcinoid tumour of the gastrointestinal tract / Extrahepatic Bile Duct Cancer / Liver Cancer / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Small Intestine Cancer1
2Unknown StatusTreatmentHead and Neck Carcinoma1
2WithdrawnTreatmentDesmoid Tumors / Fibromatosis1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2, 3CompletedNot AvailableSpinal Muscular Atrophy (SMA)1
2, 3TerminatedTreatmentDisseminated Sclerosis1
2, 3Unknown StatusTreatmentThalassemia Intermedia (TI)1
3Active Not RecruitingTreatmentEssential Thrombocythemia (ET) / Polycythemia Vera (PV) / Primary Myelofibrosis1
3Active Not RecruitingTreatmentHigh Risk Essential Thrombocythemia / High Risk Polycythemia Vera1
3Active Not RecruitingTreatmentPlasmodium Infections / Sickle Cell Disorders1
3CompletedNot AvailableEssential Thrombocythemia (ET)1
3CompletedPreventionHematologic Diseases / Sickle Cell Disorders1
3CompletedTreatmentAstrocytomas / Glioblastoma Multiforme1
3CompletedTreatmentHaemoglobinopathies congenital / Hematologic Diseases / Sickle Cell Disorders1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentLeukemias1
3CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms1
3CompletedTreatmentPolycythemia Vera (PV)2
3Not Yet RecruitingTreatmentEssential Thrombocythemia (ET) / MPN1
3Not Yet RecruitingTreatmentPlasmodium Infections / Sickle Cell Disorders1
3RecruitingPreventionSickle Cell Disorders / Strokes2
3RecruitingTreatmentAcute Promyelocytic Leukemia (APL)1
3RecruitingTreatmentSmith-Magenis Syndrome1
3TerminatedPreventionCerebrovascular Accidents / Hematologic Diseases / Hemochromatosis / Sickle Cell Disorders1
3TerminatedPreventionSickle Cell Disorders2
3TerminatedTreatmentLeukemias1
3TerminatedTreatmentPolycythemia Vera (PV)1
3Unknown StatusTreatmentCancer of the Larynx / Cancer of the Nasal Cavity / Cancer of the Oral Cavity / Cancer of the Pharynx / Paranasal Sinus Neoplasms1
3Unknown StatusTreatmentLOCALLY ADVANCED UNDIFFERENTIATED CARCINOMA NASOPHARYNGEAL TYPE UCNT1
3Unknown StatusTreatmentLeukemias4
4Active Not RecruitingTreatmentSickle Cell Disorders1
4CompletedOtherRenal Function Disorder / Sickle Cell Disorders1
4CompletedTreatmentDrepanocytic Men Treated by Hydroxyurea for the First Time1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentThrombocythemia, Hemorrhagic1
4Enrolling by InvitationTreatmentSickle Cell Disorders1
Not AvailableActive Not RecruitingNot AvailableSickle Cell Disorders1
Not AvailableActive Not RecruitingTreatmentSickle Cell Disorders / Strokes1
Not AvailableCompletedNot AvailableSickle Cell Disorders1
Not AvailableCompletedPreventionSickle Cell Disorders1
Not AvailableCompletedTreatmentAids / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentBeta-Thalassemia1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections3
Not AvailableCompletedTreatmentMyeloproliferative Disorders / Thrombocythemia1
Not AvailableCompletedTreatmentSickle Cell Disorders1
Not AvailableRecruitingNot AvailableSickle Cell Disorders1
Not AvailableRecruitingSupportive CareSickle Cell Disorders1
Not AvailableRecruitingTreatmentSickle Cell Disorders2
Pharmacoeconomics
Manufacturers
  • Bristol myers squibb co
  • Barr laboratories inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Par pharmaceutical inc
  • Roxane laboratories inc
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral200 mg/1
CapsuleOral300 mg/1
CapsuleOral400 mg/1
CapsuleOral500 mg/1
CapsuleOral500 mg
Tablet, film coatedOral100 mg
Tablet, film coatedOral1000 mg
Prices
Unit descriptionCostUnit
Hydroxyurea powder2.75USD g
Hydrea 500 mg capsule1.49USD capsule
Droxia 400 mg capsule0.97USD capsule
Droxia 300 mg capsule0.94USD capsule
Droxia 200 mg capsule0.91USD capsule
Hydroxyurea 500 mg capsule0.9USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)133-136U.S. Patent 2,705,727.
water solubility1E+006 mg/L (at 25 °C)MERCK INDEX (1996)
logP-1.80HANSCH,C ET AL. (1995)
logS1.12ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility269.0 mg/mLALOGPS
logP-1.8ALOGPS
logP-1.4ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)10.14ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area75.35 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.91 m3·mol-1ChemAxon
Polarizability5.94 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9154
Blood Brain Barrier+0.9382
Caco-2 permeable-0.7235
P-glycoprotein substrateNon-substrate0.8437
P-glycoprotein inhibitor INon-inhibitor0.9736
P-glycoprotein inhibitor IINon-inhibitor0.9946
Renal organic cation transporterNon-inhibitor0.9697
CYP450 2C9 substrateNon-substrate0.8063
CYP450 2D6 substrateNon-substrate0.8363
CYP450 3A4 substrateNon-substrate0.7784
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9077
CYP450 2D6 inhibitorNon-inhibitor0.927
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9072
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9778
Ames testAMES toxic0.8685
CarcinogenicityNon-carcinogens0.6129
BiodegradationNot ready biodegradable0.7305
Rat acute toxicity1.1524 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9846
hERG inhibition (predictor II)Non-inhibitor0.9715
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0059-3950000000-0418fbb00ea645e9e0ceView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0920000000-be691e1a11d76d687cc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-15e079ef519fdae75dabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-f39d1396b2b03d5846c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01ox-9000000000-b5fb6577ca88b375ebeaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-6093ebde62cb84552dd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as carboximidic acids and derivatives. These are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboximidic acids and derivatives
Direct ParentCarboximidic acids and derivatives
Alternative ParentsOrganopnictogen compounds / Organooxygen compounds / Imines / Hydrocarbon derivatives
SubstituentsCarboximidic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Organooxygen compound / Organonitrogen compound / Imine / Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsone-carbon compound, ureas (CHEBI:44423 ) / a small molecule (HYDROXY-UREA )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ribonucleoside-diphosphate reductase activity, thioredoxin disulfide as acceptor
Specific Function:
Provides the precursors necessary for DNA synthesis. Catalyzes the biosynthesis of deoxyribonucleotides from the corresponding ribonucleotides.
Gene Name:
RRM1
Uniprot ID:
P23921
Molecular Weight:
90069.375 Da
References
  1. Culligan K, Tissier A, Britt A: ATR regulates a G2-phase cell-cycle checkpoint in Arabidopsis thaliana. Plant Cell. 2004 May;16(5):1091-104. Epub 2004 Apr 9. [PubMed:15075397 ]
  2. Zhou B, Liu X, Mo X, Xue L, Darwish D, Qiu W, Shih J, Hwu EB, Luh F, Yen Y: The human ribonucleotide reductase subunit hRRM2 complements p53R2 in response to UV-induced DNA repair in cells with mutant p53. Cancer Res. 2003 Oct 15;63(20):6583-94. [PubMed:14583450 ]
  3. Jiang W, Xie J, Varano PT, Krebs C, Bollinger JM Jr: Two distinct mechanisms of inactivation of the class Ic ribonucleotide reductase from Chlamydia trachomatis by hydroxyurea: implications for the protein gating of intersubunit electron transfer. Biochemistry. 2010 Jun 29;49(25):5340-9. doi: 10.1021/bi100037b. [PubMed:20462199 ]
  4. Davies BW, Kohanski MA, Simmons LA, Winkler JA, Collins JJ, Walker GC: Hydroxyurea induces hydroxyl radical-mediated cell death in Escherichia coli. Mol Cell. 2009 Dec 11;36(5):845-60. doi: 10.1016/j.molcel.2009.11.024. [PubMed:20005847 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Drug created on June 13, 2005 07:24 / Updated on June 24, 2017 13:14