Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H16ClN5 |
| Molecular Weight | 253.731 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NC(=N)NC(=N)NC1=CC=C(Cl)C=C1
InChI
InChIKey=SSOLNOMRVKKSON-UHFFFAOYSA-N
InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)
Proguanil is a prophylactic antimalarial drug, which works by stopping the malaria parasite, Plasmodium falciparum and Plasmodium vivax, from reproducing once it is in the red blood cells. Proguanil in combination with atovaquone are marked under the brand name malarone, which is indicated for the treatment of acute, uncomplicated P. falciparum malaria and for the prophylaxis of Plasmodium falciparum malaria, including in areas where chloroquine resistance has been reported. Atovaquone and proguanil, interfere with 2 different pathways involved in the biosynthesis of pyrimidines required for nucleic acid replication. Atovaquone is a selective inhibitor of parasite mitochondrial electron transport. Proguanil hydrochloride primarily exerts its effect by means of the metabolite cycloguanil, a dihydrofolate reductase inhibitor. Inhibition of dihydrofolate reductase in the malaria parasite disrupts deoxythymidylate synthesis. Recently were done experiments, which confirmed the hypothesis that proguanil might act on another target than dihydrofolate reductase. In addition, was made conclusion, that effectiveness of malarone was due to the synergism between atovaquone and proguanil and may not require the presence of cycloguanil.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1939 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | MALARONE Approved UsePrevention of Malaria: Atovaquone and proguanil hydrochloride tablets are indicated for the prophylaxis of P. falciparum malaria, including in areas where chloroquine resistance has been reported (see CLINICAL STUDIES). Treatment of Malaria: Atovaquone and proguanil hydrochloride tablets are indicated for the treatment of acute, uncomplicated P. falciparum malaria. Atovaquone and proguanil hydrochloride tablets have been shown to be effective in regions where the drugs chloroquine, halofantrine, mefloquine, and amodiaquine may have unacceptable failure rates, presumably due to drug resistance. Launch Date9.6353282E11 |
|||
| Preventing | MALARONE Approved UsePrevention of Malaria: Atovaquone and proguanil hydrochloride tablets are indicated for the prophylaxis of P. falciparum malaria, including in areas where chloroquine resistance has been reported (see CLINICAL STUDIES). Treatment of Malaria: Atovaquone and proguanil hydrochloride tablets are indicated for the treatment of acute, uncomplicated P. falciparum malaria. Atovaquone and proguanil hydrochloride tablets have been shown to be effective in regions where the drugs chloroquine, halofantrine, mefloquine, and amodiaquine may have unacceptable failure rates, presumably due to drug resistance. Launch Date9.6353282E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
(4-CHLOROPHENYL)BIGUANIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
10 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
(4-CHLOROPHENYL)BIGUANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
980 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
170 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
190 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8329294/ |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PROGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
209 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8329294/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
50 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
CYCLOGUANIL blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
41 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
CYCLOGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
883 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
(4-CHLOROPHENYL)BIGUANIDE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
249 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
(4-CHLOROPHENYL)BIGUANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
14070 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2975 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
141 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8329294/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CYCLOGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
834 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
CYCLOGUANIL blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
190 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8329294/ |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
CYCLOGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
661 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
CYCLOGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
16.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3440097/ |
3.5 mg/kg bw single, oral dose: 3.5 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8329294/ |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PROGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8329294/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PROGUANIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
100 mg 2 times / day multiple, oral Recommended Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Co-administed with:: chloroquine(155 mg; oral; 2/week) Sources: Page: p.1891 |
healthy, 13–74 n = 511 Health Status: healthy Condition: malaria prophylaxis Age Group: 13–74 Sex: M+F Population Size: 511 Sources: Page: p.1891 |
Disc. AE: Abdominal pain, Diarrhea... AEs leading to discontinuation/dose reduction: Abdominal pain (0.98%) Sources: Page: p.1891Diarrhea (0.78%) Nausea (1.17%) Vomiting (0.39%) |
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Co-administed with:: atovaquone(250 mg oral; 1/day) Sources: Page: p.745 |
healthy, 16 - 65 n = 175 Health Status: healthy Condition: malaria prophylaxis Age Group: 16 - 65 Sex: M+F Population Size: 175 Sources: Page: p.745 |
Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (1.14%) Sources: Page: p.745 |
150 mg 1 times / day multiple, oral (max) Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: chloroquine(77.5-310 mg; oral; 1/week) Sources: Page: p.1720 |
healthy, 3–16 n = 111 Health Status: healthy Condition: malaria prophylaxis Age Group: 3–16 Sex: M+F Population Size: 111 Sources: Page: p.1720 |
Disc. AE: Abdominal pain, Nausea... AEs leading to discontinuation/dose reduction: Abdominal pain (grade 1-2, 1.8%) Sources: Page: p.1720Nausea (grade 1-3, 1.8%) |
200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
Other AEs: Hair loss, Skin scaly... Other AEs: Hair loss Sources: Skin scaly Scales Aphthous ulcer Hematologic disorder |
200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
Other AEs: Epigastric discomfort, Vomiting... Other AEs: Epigastric discomfort Sources: Vomiting |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Vomiting | 0.39% Disc. AE |
100 mg 2 times / day multiple, oral Recommended Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Co-administed with:: chloroquine(155 mg; oral; 2/week) Sources: Page: p.1891 |
healthy, 13–74 n = 511 Health Status: healthy Condition: malaria prophylaxis Age Group: 13–74 Sex: M+F Population Size: 511 Sources: Page: p.1891 |
| Diarrhea | 0.78% Disc. AE |
100 mg 2 times / day multiple, oral Recommended Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Co-administed with:: chloroquine(155 mg; oral; 2/week) Sources: Page: p.1891 |
healthy, 13–74 n = 511 Health Status: healthy Condition: malaria prophylaxis Age Group: 13–74 Sex: M+F Population Size: 511 Sources: Page: p.1891 |
| Abdominal pain | 0.98% Disc. AE |
100 mg 2 times / day multiple, oral Recommended Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Co-administed with:: chloroquine(155 mg; oral; 2/week) Sources: Page: p.1891 |
healthy, 13–74 n = 511 Health Status: healthy Condition: malaria prophylaxis Age Group: 13–74 Sex: M+F Population Size: 511 Sources: Page: p.1891 |
| Nausea | 1.17% Disc. AE |
100 mg 2 times / day multiple, oral Recommended Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Co-administed with:: chloroquine(155 mg; oral; 2/week) Sources: Page: p.1891 |
healthy, 13–74 n = 511 Health Status: healthy Condition: malaria prophylaxis Age Group: 13–74 Sex: M+F Population Size: 511 Sources: Page: p.1891 |
| Headache | 1.14% Disc. AE |
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Co-administed with:: atovaquone(250 mg oral; 1/day) Sources: Page: p.745 |
healthy, 16 - 65 n = 175 Health Status: healthy Condition: malaria prophylaxis Age Group: 16 - 65 Sex: M+F Population Size: 175 Sources: Page: p.745 |
| Abdominal pain | grade 1-2, 1.8% Disc. AE |
150 mg 1 times / day multiple, oral (max) Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: chloroquine(77.5-310 mg; oral; 1/week) Sources: Page: p.1720 |
healthy, 3–16 n = 111 Health Status: healthy Condition: malaria prophylaxis Age Group: 3–16 Sex: M+F Population Size: 111 Sources: Page: p.1720 |
| Nausea | grade 1-3, 1.8% Disc. AE |
150 mg 1 times / day multiple, oral (max) Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Co-administed with:: chloroquine(77.5-310 mg; oral; 1/week) Sources: Page: p.1720 |
healthy, 3–16 n = 111 Health Status: healthy Condition: malaria prophylaxis Age Group: 3–16 Sex: M+F Population Size: 111 Sources: Page: p.1720 |
| Aphthous ulcer | 200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
|
| Hair loss | 200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
|
| Hematologic disorder | 200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
|
| Scales | 200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
|
| Skin scaly | 200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
|
| Epigastric discomfort | 200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
|
| Vomiting | 200 mg 2 times / day multiple, oral (max) Overdose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: P. falciparum malaria Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [Ki 6.76 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 2, 11, (Label) 15, (PMDA_A100_1 in Japanese) 22 |
major | |||
| no | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A case of recurrent subacute disseminated intravascular coagulation associated with malarial prophylaxis. | 1975 Jan 25 |
|
| Neuromyopathy associated with amodiaquine hydrochloride. | 1987 Oct 1 |
|
| In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs. | 1990 Aug |
|
| Chloroquine-induced mania. | 1991 Jul |
|
| Mefloquine. | 1993 Jun 19 |
|
| Effect of atovaquone and atovaquone drug combinations on prophylaxis of Pneumocystis carinii pneumonia in SCID mice. | 1995 Apr |
|
| Adverse effects and compliance with mefloquine or proguanil antimalarial chemoprophylaxis. | 1997 |
|
| Atovaquone-proguanil versus chloroquine-proguanil for malaria prophylaxis in non-immune travellers: a randomised, double-blind study. Malarone International Study Team. | 2000 Dec 2 |
|
| Seizures after antimalarial medication in previously healthy persons. | 2000 May-Jun |
|
| Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. | 2001 Jan |
|
| A trial of proguanil-dapsone in comparison with sulfadoxine-pyrimethamine for the clearance of Plasmodium falciparum infections in Tanzania. | 2001 Jul-Aug |
|
| [Many travellers suffer of side-effects of malaria prophylaxis]. | 2002 Jun 27 |
|
| Severe mucocutaneous necrotizing vasculitis associated with the combination of chloroquine and proguanil. | 2003 |
|
| Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Acute hepatitis and atovaquone/proguanil. | 2005 Sep-Oct |
|
| The risk of antimalarials in patients with renal failure. | 2007 Dec |
|
| In vitro atovaquone/proguanil susceptibility and characterization of the cytochrome b gene of Plasmodium falciparum from different endemic regions of Thailand. | 2008 Jan 28 |
Sample Use Guides
The daily dose should be taken at the same time each day with food or a milky drink. In the event of vomiting within 1 hour after dosing, a repeat dose should be taken.
Prevention of Malaria: start prophylactic treatment with MALARONE (atovaquone and proguanil hydrochloride) 1 or 2 days before entering a malaria-endemic area and continue daily during the stay and for 7 days after return. Adults: One MALARONE Tablet (adult strength = 250 mg atovaquone/100 mg proguanil hydrochloride) per day. Pediatric Patients: The dosage for prevention of malaria in pediatric patients is based upon body weight.
Treatment of Acute Malaria Adults: four malarone tablets (adult strength; total daily dose 1 g atovaquone/400 mg proguanil hydrochloride) as a single daily dose for 3 consecutive days. Pediatric Patients: The dosage for treatment of acute malaria in pediatric patients is based upon body weight.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: The in vitro effect of proguanil and its active metabolite cycloguanil on proliferating human blood mononuclear cells was studied. Proguanil had no effect on 14C-thymidine incorporation or on the number of cells. Cycloguanil, in concentrations corresponding to the plasma levels found in clinical practice, blocked the endogenous synthesis of thymidine and decreased the number of mitogen- and antigen-stimulated cells.
Unknown
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C271
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NDF-RT |
N0000000191
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NDF-RT |
N0000175482
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LIVERTOX |
NBK548239
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WHO-ATC |
P01BB01
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NCI_THESAURUS |
C2153
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WHO-ESSENTIAL MEDICINES LIST |
6.5.3.2
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WHO-ATC |
P01BB51
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NDF-RT |
N0000000191
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m3361
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PROGUANIL
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DB01131
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8455
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100000081142
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SUB10079MIG
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2282
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4923
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2382
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S61K3P7B2V
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418
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500-92-5
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D002727
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C61907
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S61K3P7B2V
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CHEMBL1377
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207-915-6
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DTXSID3022794
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METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PRODRUG)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD
